SU259895A1 - METHOD OF OBTAINING 2- (y-KETOALKENYL)-DERIVATIVES OF MERCAPTOBENZTHIAZOLE - Google Patents
METHOD OF OBTAINING 2- (y-KETOALKENYL)-DERIVATIVES OF MERCAPTOBENZTHIAZOLEInfo
- Publication number
- SU259895A1 SU259895A1 SU1250515A SU1250515A SU259895A1 SU 259895 A1 SU259895 A1 SU 259895A1 SU 1250515 A SU1250515 A SU 1250515A SU 1250515 A SU1250515 A SU 1250515A SU 259895 A1 SU259895 A1 SU 259895A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mercaptobenzthiazole
- derivatives
- ketoalkenyl
- obtaining
- mol
- Prior art date
Links
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- GAQRZTCWAYLSKR-UHFFFAOYSA-N 1-(2-chlorophenyl)prop-2-en-1-one Chemical group ClC1=CC=CC=C1C(=O)C=C GAQRZTCWAYLSKR-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
Изобретение относитс к области получени 2- (Y - катоалкенил) -производных меркаптобензтиазола , которые могут найти применение в качестве ускорителей вулканизаци каучука , а также физиологически активных веществ и полупродуктов дл органического синтеза.The invention relates to the field of the production of 2- (Y-catoalkenyl) mercaptobenzthiazole derivatives, which can be used as accelerators for the vulcanization of rubber, as well as physiologically active substances and intermediates for organic synthesis.
Предлагаемый способ получени 2-(у-кетоалкенил ) -производных меркаптобенз11иазола заключаетс в том, что арил-В-хлорвинилкетон подвергают взаимодействию с 2-меркаптобензтиазолом при нагревании до температуры кипени вод ной бани в среде органического растворител , предпочтительно безводного, с последующим выделением продуктов известным способом.The proposed method for the preparation of 2- (y-ketoalkenyl) mercaptobenzenelazole derivatives consists in the fact that the aryl-B-chlorovinyl ketone is reacted with 2-mercaptobenzthiazole when heated to the boiling point of a water bath in an organic solvent, preferably anhydrous, followed by isolation of products with known in a way.
Выход 50-700/0.Output 50-700 / 0.
Пример 1. 1-(2-меркаптобензтиазол)-2бензоилэтилен .Example 1. 1- (2-mercaptobenzthiazole) -2-benzoylethylene.
(0.018 моль 2-меркаптобензтиазола и Зг (0.018 моль фенил-р-хлорвинилкетона в 100 мл безводного бензола кип т т при тщательном перемешивании в течение 1 час. Выпадает желтый порошкообразный осалок с т. пл. 120°С (толуол). Выход 2,9 г (55%). (0.018 mol of 2-mercaptobenzthiazole and 3g (0.018 mol of phenyl-p-chlorovinyl ketone in 100 ml of anhydrous benzene is boiled with thorough stirring for 1 hour. A yellow powder of saline with a mp of 120 ° C (toluene) drops out. Yield 2 , 9 g (55%).
Найдено, о/,: с 64,76; 64,88; Н 3.76: 369: N 4,99; S 21.50; 21,30.Found, o /, with 64.76; 64.88; H 3.76: 369: N 4.99; S 21.50; 21.30.
Пример 2. 1-(2-меркаптобензт1иазол)-2 (о-хлорбензоил)-этилен получают из 2.3 г (0,014 моль 2-меркаптобензтиазола и 3 г (0.014 юль о-хлорфенил-В-хлорвинилкетона в 100 мл толуола при нагревании в течение 1 час до 100°С. Получают желтый кристаллический осалок с т. пл. 192°С (дихлорэтан).Example 2. 1- (2-mercaptobenzt1iazol) -2 (o-chlorobenzoyl) -ethylene is obtained from 2.3 g (0.014 mol of 2-mercaptobenzthiazole and 3 g (0.014 g of o-chlorophenyl-B-chlorovinyl ketone in 100 ml of toluene when heated for 1 hour to 100 ° C. A yellow crystalline oil with a mp of 192 ° C (dichloroethane) is obtained.
Выход 3.5 г (71Vn).Yield 3.5 g (71Vn).
Найдено, о/о: С 57.86; 58.07: Н 3,13; 2.91; С1 10.88: 11.02: S 19.66: 19,71.Found, o / o: C 57.86; 58.07: H 3.13; 2.91; C1 10.88: 11.02: S 19.66: 19.71.
Ci.H,nClNOS,.Ci.H, nClNOS ,.
Вычислено. %: Calculated. %:
С 57.91: Н 3.01; С 10.70; S 19.31.C 57.91: H 3.01; C, 10.70; S 19.31.
Принтер 3. 1-(2- тepкaптoбeнзтиaзoл)-2 (т-х.лорбензоил)-этилен - получают из 2.3 г (О.ОМ моль 2-меркаптобензотиазола и 3 г (0.014 , п-хлорфенил-В-хлор.виннлкетона в 70 мл безводного толуола при нагревании до . После отгонки растворител выпадают кристаллы с т. пл. 93-94°С (ТОЛУОЛ).Printer 3. 1- (2-tercaptobenzthiazol) -2 (t.h.orbenzoyl) -ethylene is prepared from 2.3 g (O.OM mole 2-mercaptobenzothiazole and 3 g (0.014, p-chlorophenyl-B-chlorine-vinclinketone in 70 ml of anhydrous toluene when heated to. After the solvent has been distilled off, crystals with mp 93-94 ° C (TOLUOL) precipitate.
Выход 3.8 г (770/,-).Yield 3.8 g (770 /, -).
Найдено, о/,: С 58.11: 58.01: Н 3.42: 3.07; С1 10.90: 0.65; N 4.59: S 19.19: 19,34.Found, o / ,: C 58.11: 58.01: H 3.42: 3.07; C1 10.90: 0.65; N 4.59: S 19.19: 19,34.
CtrHi.ClNOSo.CtrHi.ClNOSo.
Вычислено, о/п: С 57,91: Н 3.01: С1 10.70; N 4.22: S 19.31.Calculated, o / p: C 57.91: H 3.01: C1 10.70; N 4.22: S 19.31.
60 мл безводного ксилола, 60 ml of anhydrous xylene,
Получают желтое с т. пл. 75°С (токристаллическое вещество луол). Выход 3,2 5 (71о/о).Get yellow with so pl. 75 ° C (tocrystalline substance luol). Yield 3.2 5 (71o / o).
Найдено, %: С 51,46; 51,74; Found,%: C 51.46; 51.74;
Н 2,44; 2,07; Вг 21,30; 21,71; N 4,02; 3,98; S 17,08; 16,55.H 2.44; 2.07; Br 21.30; 21.71; N 4.02; 3.98; S 17.08; 16.55.
iCieHioBrNOSz.iCieHioBrNOSz.
.Вычислено, о/о: :С 51,07; Н 1,66; Вг 21,25; N 3,72; S 17,02.. Calculated, o / o: S 51.07; H 1.66; Br 21.25; N 3.72; S 17.02.
Пример 5. 1-(2-меркантобенз11иазол)-2 (и-бромбензоил)-этилен иолучают из 3 г (0,012 моль} л-бром-|3-хлорвинилкетона и 2 г (0,012 моль} 2-меркаитобензт1иазола в 60 мл безводного бензола. Получают желтое кристаллическое вещество с т. нл. 201°С (дихлорэтан ). Выход 3,9 г (93о/о).Example 5. 1- (2-mercantobenz11iazol) -2 (and-bromobenzoyl) -ethylene is obtained from 3 g (0.012 mol} l-bromo- | 3-chlorovinyl ketone and 2 g (0.012 mol) 2-merkaitobenz1azole in 60 ml anhydrous benzene A yellow crystalline substance is obtained with a temperature of 201 ° C. (dichloroethane). The yield is 3.9 g (93 ° / o).
Найдено, о/,,: с 51,51; 51,53; Н 2,44; 2,59; Вг 21,41; S 17,11; 17,30.Found, o / ,,: with 51,51; 51.53; H 2.44; 2.59; Br 21.41; S 17.11; 17.30.
CieHioBrNOSa.CieHioBrNOSa.
Вычислено, о/о: С 51,07; Н 2,66; Вг 21,25; S 17,02.Calculated, o / o: C 51.07; H 2.66; Br 21.25; S 17.02.
Пример 6. 1 - (2-меркантобензти азол) -2 ( - итробензо.ил)-этилен получают из 3,5 г (0,016 моль) -нитро-р-хлорвинилкетона иExample 6. 1 - (2-mercantobenzene azole) -2 (- itrobenzo.yl) -ethylene is obtained from 3.5 g (0.016 mol) -nitro-p-chlorovinyl ketone and
2,6 г (0,016 моль} 2-меркаптобензтиазола в 50 мл бензола. Получают кристаллическое вещество с т, пл. 225°С (дихлорэтан).2.6 g (0.016 mol} of 2-mercaptobenzthiazole in 50 ml of benzene. A crystalline substance is obtained, having a melting point of 225 ° C (dichloroethane).
Выход 4 г (71%).Yield 4 g (71%).
Найдено, %: С 56,44; 56,38; Н 2,85; 2,56; N 7,98; 8,32; S 19,02; 18,68.Found,%: With 56.44; 56.38; H 2.85; 2.56; N 7.98; 8.32; S 19.02; 18.68.
CieHioN2O3S2.CieHioN2O3S2.
Вычислено, о/о: С 56,14; Н 2,92; N 8,17; S 18,71.Calculated, o / o: C 56.14; H 2.92; N 8.17; S 18.71.
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU259895A1 true SU259895A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9873705B2 (en) | 2015-10-02 | 2018-01-23 | The Trustees Of Dartmouth College | Vinylogous thioester compounds and methods of use |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9873705B2 (en) | 2015-10-02 | 2018-01-23 | The Trustees Of Dartmouth College | Vinylogous thioester compounds and methods of use |
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