SU1266849A1 - Macrocyclic bisazoresorcinols of undeca-,tetradeca-,heptadeca-dien systems - Google Patents
Macrocyclic bisazoresorcinols of undeca-,tetradeca-,heptadeca-dien systems Download PDFInfo
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- SU1266849A1 SU1266849A1 SU853850035A SU3850035A SU1266849A1 SU 1266849 A1 SU1266849 A1 SU 1266849A1 SU 853850035 A SU853850035 A SU 853850035A SU 3850035 A SU3850035 A SU 3850035A SU 1266849 A1 SU1266849 A1 SU 1266849A1
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- tetradeca
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- undeca
- macrocyclic
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- PEUHBSAKNWEJHZ-FNORWQNLSA-N (3e)-heptadeca-1,3-diene Chemical compound CCCCCCCCCCCCC\C=C\C=C PEUHBSAKNWEJHZ-FNORWQNLSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 229960001755 resorcinol Drugs 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MKODCDSZZKDPMN-UHFFFAOYSA-N 2-[1-(2-aminophenoxy)ethoxy]aniline Chemical compound C=1C=CC=C(N)C=1OC(C)OC1=CC=CC=C1N MKODCDSZZKDPMN-UHFFFAOYSA-N 0.000 description 1
- WBRJWBVUQGHOQY-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]aniline Chemical compound CCOCCOCCOC1=CC=CC=C1N WBRJWBVUQGHOQY-UHFFFAOYSA-N 0.000 description 1
- -1 2-amino-5-nitro-phenoxy Chemical group 0.000 description 1
- RTIJKNBQBBLERG-UHFFFAOYSA-N CC(OC(C)OC(C=CC=C1)=C1N)OC(C=CC=C1)=C1N Chemical compound CC(OC(C)OC(C=CC=C1)=C1N)OC(C=CC=C1)=C1N RTIJKNBQBBLERG-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- USXWDUPSQMFPAR-UHFFFAOYSA-N NC1=C(OC(C)(C)OC2=C(C=CC=C2)N)C=CC=C1 Chemical compound NC1=C(OC(C)(C)OC2=C(C=CC=C2)N)C=CC=C1 USXWDUPSQMFPAR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
МАКРОЦИЮМЧЕСКИЕ БИСАЗОРЕЗОРЦИНЫ СИСТЕМ УНДЕКА-, ТЕТРАДЕКА-, ГЕПТАДЕКАДИЕНА общей формулы в которой, когда X - кислород, R группа , -СНгСН -, .,-, -СНгСНгОСНгСН-гСНг СН,.СН.ОСН г , R-H NOj- , SO,H или когда X - сера, R - группа -СН СН R-H , .MACRO-RESEARCHES OF UNDECA, TETRADECA, HEPTADECADIENE SYSTEMS of the general formula in which, when X is oxygen, R group, -СНСНН,. or when X is sulfur, R is the group -CH CH RH,.
Description
hO 0d 9d X 4 CO Изобретение относитс к области органической химии, в частности к новому классу бисазорезорцинов макродиклических бисазорезорцинов систем ундека-, тетрадека-, гептадекадиена общей формулы он Б соторой, когда X - кислород, R группа - СНгСН-г, -Cl-I CH,jCH-, , R-H, NO, Н, или когда X - сера, R - группа - СН..,СН, R- Н, R Н. Цель изобретени - новые макроциклические бисазорезорцины,которые могут найти применение в качестве экстрагентов и фотометрических реагентов на ионы щeJroчныx металлов. Пример 1 . Получение 1 диокси-2 ,3,10,11-тетрааза-5,8-диок 1(2,4)фена-4,9(1,2)дифена-циклоунд 2,10-диена, Суспензию 0,25 г (1 ммоль) бис (2-аминофенокси) этана в 10 мл 2,5 I1C1 диазотируют 1 мл 5 Ы раствора NaN02 при 0°С, перемешивают 30 мин и избыток HN02 удал ют сульфаминопой кислотой, К 500 мл содового ра вора при 5 С добавл ют одновременн по капл м paзбaвлetи ый до 50 мл ра вор соли диазони и раствор 0,11 г (1 ммоль) резорцина в 50 №i воды. Кислотность среды в течение реакци поддерживаетс 9,0-9,5. Осадок отд л ют, экстрагируют хлороформом и х матографируют на колонке с силикаг лем. Вьщелено 0,01 г (3%), т.пл.27 274 С (после перекристаллизации из бензола) . . Найдено ,%: С 63,86; Н 4,24, N 14,44.Масс-спектр М 376.. CwHigN O,. . Вычислено,%: С 63,82, Н 4,28; N 14,89. УФ-спектр (в спирте).А/на ( IgE): 416(4,38). ИК-спектр (9,см 1408 () 1270, 1108(С-0-С). Пример 2. Получение 1 диокси-2,3,11,12-тетрааза-5,9гдиокса1 (2,4)фена-4,10(1,2)дифена-циклододека-2 ,11-диена. Соединение получают аналогично из бис(2-аминофенокси) пропана и резорцина . Вьщелено 0,05 г (13%), т.пл. 247-248 С (из бензола). Найдено,%: С 64,55; Н 4,66, N 14,38. Масс-спектр . С2, H,gN404. Вычислено,%: С 64,61 Н 4,65; N 14,35; УФ-спектр (в спирте), AMotcdgE): 426,7(4,54). ИК-спектр (,см): 1408(), 1261, 1110(С-0-С). Пример 3. Получение l диокси-2 ,3,13,14-тетрааза-5,8-11, триокса-1(2,4)фена-4,12 (1,2)дифенапиклотетрадека-2513-диена . Соединение получают аналогично из бис(2-аминофенокси)-3-оксапентана и резорцина. Выход 52%, т.пл. 278279 С (из ацетона). Найдепо,%: С 62,74, Н 4,82, N 13,19%. Масс-спектр . Вычислено,%: С 62,85; Н 4,79; N 13,33%. УФ-спектр (в спирте), mqKcClgE): 430,4(4,49). ИК-спектр (,см-): 1409 (), 1266, 1113 (С-О-С). Пример 4. Получение 1 диокси-2 ,3,16,17-тетрааза-5,8,11,14тетраокса-1 (2,4)фена-4,15(1,2)дифена-циклогептадека-2 ,16-диена. Соединение получают аналогично из 1,8-бйс(2-аминофенокси)-3,6-диоксаоктана и резорцина. Выход 54%, т.пл. 208-209С (из бензола). Найдено,%: С 62,05; Н 5,27/ N 12,07. Масс-спектр . H,,, Вычислено,%: С 62,06; Н 5,21; N 12,06. УФ-спектр (в спирте); , x(lgE): 417,5(4,55). ИК-спектр (, : 1408 (), 1260,1 111 (С-О-С). П р им е р 5. Получение Г диокси-2 ,3,10,11-тетрааза-5,8-дитиа1 (2;4)фена-4,9(1,2)дифена-циклоундека-2 ,10-диена. Соединение получают аналогично из бис(2-аминофентио)этана и резорцина . Выход 20%, т.пл.- 275-277°С (из бензола). Найдено,%: С 58,92$ Н 3,91; N 13,68, S 15,73. Масс-спектр м408. CaoM.. Вычислено, С 58,80, Н 3,95; N 13,71 j S 15,-70, УФ-спектр (в спи те),А«,, (IgE): 411,3(4,48). ИК-спектр (Ч,см ): 1401 (). Пример 6. Получение окси-2,3,13,14-тетрааза-5,8,11-три окса-1(2,4)фена-4,12(1,2)(5,5-динитpo )дифeнaциклoтeтpaдeкa-2, 13-ди на. Соединение получают аналогично из 1,5-бис(2-амино-5-нитро-фенокси 3-оксапентана и резорцина. Выход 35%, т.пл, 300°С. ,Найдено,%: С 51,76i Н 3,83j N 15,93. Масс-спектр . C,jH (д .. Вычислено,%: С 51,77J H3,55j N 16,16. УФ-спектр (в хлоро форме) ,,o(lgE) : 426,7(4,66), 536,7(4,38). ИК-спектр (,): 1417 (), 1347(Ы02-симм.), 1260, 1122(С-0-С). 7. Получение и м е р сульфо-1 -диокси-2,3,13,14-тeтpaaзa-тeтpaaзa-5 ,8, 11-триокса-1(2,4) фена-4,12(1,2)дифена-циклотетрадека2 ,13-диена. Соединение получаетс аналогично из 1,5-бис(2-аминофекси)-3-оксапентана и Ма-йоли 4-сульфорезорцина. Выход 56%, т.пл. 300С. Найдено,%: С 49,17; Н 3,81; N 1б,,26, S 5,73, Cj2H2pN40,SNa . Вьгчислено,%: С 48,89; Н 3,92; N 10,37} S 5,93. УФ-спектр (в воде). „„,e(lgE): 438(4,61).hO 0d 9d X 4 CO The invention relates to the field of organic chemistry, in particular, to a new class of bisazorezorecins of macroscopic bisazorezorens of the systems undeca-, tetradeca-, heptadecadiene of the general formula he B, when X is oxygen, R group is SNHCH-g, -Cl- I CH, jCH-, RH, NO, H, or when X is sulfur, R is a group — CH., CH, R — H, R N. The purpose of the invention is new macrocyclic bisazorezorecins that can be used as extractants. and photometric reagents for ions of alkaline metals. Example 1 Getting 1 dioxy-2, 3,10,11-tetraaz-5,8-diox 1 (2,4) phen-4,9 (1,2) diphen-cyclound 2,10-diene, Suspension 0.25 g ( 1 mmol) bis (2-aminophenoxy) ethane in 10 ml of 2.5 I1C1 is diazotized with 1 ml of 5 Na solution of NaN02 at 0 ° C, stirred for 30 minutes and excess HN02 is removed by sulfamic acid, To 500 ml of soda water at 5 ° C Simultaneously, drop by drop, dilute to 50 ml of a solution of a diazonium salt and a solution of 0.11 g (1 mmol) of resorcinol in 50 №i of water. The acidity of the medium during the reaction is maintained from 9.0 to 9.5. The precipitate is separated, extracted with chloroform, and x chromatographed on a silica gel column. 0.01 g (3%) was added, mp 277 ° C (after recrystallization from benzene). . Found,%: C 63.86; H 4.24, N 14.44. Mass spectrum M 376 .. CwHigN O ,. . Calculated,%: C, 63.82; H, 4.28; N 14.89. UV spectrum (in alcohol) .A / a (IgE): 416 (4.38). IR spectrum (9, cm 1408 () 1270, 1108 (C-0-C). Example 2. Preparation of 1 dioxy-2,3,11,12-tetraase-5.9 gdiox1 (2.4) phen-4, 10 (1,2) diphen-cyclododeca-2, 11-diene. The compound is prepared similarly from bis (2-aminophenoxy) propane and resorcin. 0.05 g (13%) is isolated, mp 247-248 C (from benzene. Found:% C 64.55; H 4.66, N 14.38. Mass spectrum. C2, H, gN404. Calculated: C 64.61 H 4.65; N 14.35; UV spectrum (in alcohol), AMotcdgE): 426.7 (4.54). IR (cm): 1408 (), 1261, 1110 (C-0-C). Example 3. Getting l dioxy-2, 3,13,14-tetraaz-5,8-11, triox-1 (2,4) phen-4,12 (1,2) diphenapiclotetradec-2513-diene. The compound is prepared analogously from bis (2-aminophenoxy) -3-oxapentane and resorcin. Yield 52%, mp. 278279 С (from acetone). Found%: C 62.74, H 4.82, N 13.19%. Mass spectrum. Calculated,%: C, 62.85; H 4.79; N 13.33%. UV spectrum (in alcohol), mqKcClgE): 430.4 (4.49). IR spectrum (cm-): 1409 (), 1266, 1113 (C-O-C). Example 4. Obtaining 1 dioxy-2, 3,16,17-tetraaz-5,8,11,14 tetraox-1 (2,4) phen-4,15 (1,2) diphen-cycloheptadec-2, 16-diene . The compound is prepared analogously from 1,8-bys (2-aminophenoxy) -3,6-dioxaoctane and resorcin. Yield 54%, mp. 208-209С (from benzene). Found,%: C 62.05; H 5.27 / N 12.07. Mass spectrum. H ,,, Calculated,%: C 62.06; H 5.21; N 12.06. UV spectrum (in alcohol); , x (lgE): 417.5 (4.55). IR spectrum (,: 1408 (), 1260.1 111 (С-О-С). Example 5: Preparation of D-2, 3,10,11-tetraase-5,8-dithia1 (2 4) phen-4,9 (1,2) difen-cycloundek-2, 10-diene. The compound is obtained similarly from bis (2-aminofentio) ethane and resorcin. Yield 20%, mp. - 275-277 ° C (from benzene). Found: C 58.92 $ H 3.91; N 13.68, S 15.73; Mass spectrum m408. CaoM. Calculated, C 58.80, H 3.95; N 13.71 j S 15, -70, UV spectrum (in the water), A «, (IgE): 411.3 (4.48). IR spectrum (H, cm): 1401 (). Example 6. Obtaining oxy-2,3,13,14-tetraaz-5,8,11-three oxa-1 (2,4) phen-4,12 (1,2) (5,5-dinitro) difenocyclototetradec- 2, 13-di. The compound is prepared analogously from 1,5-bis (2-amino-5-nitro-phenoxy 3-oxapent on and resorcin. Yield 35%, mp, 300 ° C., Found,%: C, 51.76i H, 3.83j N, 15.93. Mass spectrum. C, jH (d. 51.77J H3.55j N 16.16. UV spectrum (in chloroform) ,, o (lgE): 426.7 (4.66), 536.7 (4.38). IR spectrum (,) : 1417 (), 1347 (L02-symm.), 1260, 1122 (C-0-C). 7. Preparation and measurement of sulfo-1-dioxy-2,3,1,1,14-tetraaza-tetrapaaza-5 , 8, 11-triox-1 (2,4) phen-4,12 (1,2) diphene-cyclotetradec 2, 13-diene. The compound is prepared analogously from 1,5-bis (2-aminifex) -3-oxapentane and Ma-yoli 4-sulforezorecin. Yield 56%, mp. 300C. Found,%: C 49.17; H 3.81; N 1b ,, 26, S 5.73, Cj2H2pN40, SNa. Incl.%: C 48.89; H 3.92; N 10.37} S 5.93. UV spectrum (in water). „„, E (lgE): 438 (4.61).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853850035A SU1266849A1 (en) | 1985-01-31 | 1985-01-31 | Macrocyclic bisazoresorcinols of undeca-,tetradeca-,heptadeca-dien systems |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853850035A SU1266849A1 (en) | 1985-01-31 | 1985-01-31 | Macrocyclic bisazoresorcinols of undeca-,tetradeca-,heptadeca-dien systems |
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| Publication Number | Publication Date |
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| SU1266849A1 true SU1266849A1 (en) | 1986-10-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| SU853850035A SU1266849A1 (en) | 1985-01-31 | 1985-01-31 | Macrocyclic bisazoresorcinols of undeca-,tetradeca-,heptadeca-dien systems |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7432371B2 (en) | 2002-02-07 | 2008-10-07 | Covalent Partners, Llc | Nanofilm and membrane compositions |
| US7595368B2 (en) | 2002-09-17 | 2009-09-29 | Covalent Partners, Llc | Nanofilm compositions with polymeric components |
| US7767810B2 (en) | 2002-02-07 | 2010-08-03 | Covalent Partners, Llc | Macrocyclic modules comprising linked cyclic synthon units for use in the formation of selectively permeable membranes |
| US8182695B2 (en) | 2003-08-06 | 2012-05-22 | Whiteford Jeffery A | Bridged macrocyclic module compositions |
-
1985
- 1985-01-31 SU SU853850035A patent/SU1266849A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Авторское свидетельство СССР № 1139730, кл. С 07 D 273/00, 1983. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7432371B2 (en) | 2002-02-07 | 2008-10-07 | Covalent Partners, Llc | Nanofilm and membrane compositions |
| US7767810B2 (en) | 2002-02-07 | 2010-08-03 | Covalent Partners, Llc | Macrocyclic modules comprising linked cyclic synthon units for use in the formation of selectively permeable membranes |
| US8110679B2 (en) | 2002-02-07 | 2012-02-07 | Covalent Partners Llc | Nanofilm and membrane compositions |
| US7595368B2 (en) | 2002-09-17 | 2009-09-29 | Covalent Partners, Llc | Nanofilm compositions with polymeric components |
| US8182695B2 (en) | 2003-08-06 | 2012-05-22 | Whiteford Jeffery A | Bridged macrocyclic module compositions |
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