SU189874A1 - METHOD OF OBTAINING | 3-Arylthioethyl B esters of N-aryldithiocarbamate Acids - Google Patents
METHOD OF OBTAINING | 3-Arylthioethyl B esters of N-aryldithiocarbamate AcidsInfo
- Publication number
- SU189874A1 SU189874A1 SU1052342A SU1052342A SU189874A1 SU 189874 A1 SU189874 A1 SU 189874A1 SU 1052342 A SU1052342 A SU 1052342A SU 1052342 A SU1052342 A SU 1052342A SU 189874 A1 SU189874 A1 SU 189874A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- arylthioethyl
- esters
- acids
- aryldithiocarbamate
- obtaining
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 3
- 150000007513 acids Chemical class 0.000 title description 3
- 150000002148 esters Chemical class 0.000 title description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 aryl isothiocyanates Chemical class 0.000 description 2
- 230000003197 catalytic Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N Phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
Пзобретение относитс к способу получени неописанных ранее (3-арилтиоэтиловых эфиров N-арилдитиокарбампповых кислот общей формулыThe invention relates to a process for the preparation of non-previously described (3-arylthioethyl esters of N-aryldithiocarbampic acids of the general formula
ArNH-C-S-CHj-CHa- ArNH-C-S-CHj-CHa-
X .., -ХX .., -X
где Ar - незамещенный или замещенный фенил или нафтил; R - алкил, алкоксил, галоид; п 0-5.where Ar is unsubstituted or substituted phenyl or naphthyl; R is alkyl, alkoxy, halogen; p 0-5.
Предлагаетс указанные соединени получать взаимодействием 5-арилтиоэтилмеркаптанов с арилизотиоцианатами.These compounds are proposed to be prepared by reacting 5-arylthioethyl mercaptans with aryl isothiocyanates.
Реакцию провод т при нагревании смеси реагентов до 100-140°С в течение 15-20 час. В более м гких услови х-при 70-90°С.The reaction is carried out by heating the mixture of reagents to 100-140 ° C for 15-20 hours. Under milder conditions, at 70-90 ° C.
Конденсацию осуществл ют в присутствии каталитических количеств (0,1-3 мол. %) третичных оснований, например триэтиламина или пиридина. Процесс завершаетс за 0,4- 3 час, целевые продукты получают с количественным выходом. Реакцию можно проводить как без растворител , ак и в обыч:1ых органических растворител х, например бензоле.The condensation is carried out in the presence of catalytic amounts (0.1-3 mol%) of tertiary bases, for example triethylamine or pyridine. The process is completed in 0.4-3 hours, the desired products are obtained in quantitative yield. The reaction can be carried out as without solvent, ak and in usual: 1st organic solvents, for example benzene.
Смесь 13,5 г (0,1 г моль) фенилизотиоцианата , 17 г (0,1 г моль) р-фенилтиоэтилмеркаитана и 0,1 г (1% мол.) триэтиламина нагревают нри 80-85°С в течение 2,5 час. Реакционную массу охлаждают и получают 30,5 г (100%) кристаллического вещества с т. пл. 93-94°С, после перекристаллизации из иетролейного эфира т. ил. 94-94,5°С.A mixture of 13.5 g (0.1 g mol) of phenyl isothiocyanate, 17 g (0.1 g mol) of p-phenylthioethyl mercovine and 0.1 g (1 mol%) of triethylamine is heated at 80-85 ° C for 2.5 hour. The reaction mass is cooled and receive 30.5 g (100%) of a crystalline substance with so pl. 93-94 ° C, after recrystallization from ethereal ether, t. Il. 94-94.5 ° C.
Найдено, %: N 4,19; S 31,70. CisHisNSg.Found,%: N 4,19; S 31.70. CisHisNSg.
Вычнслено, %: N 4,59; S 31,48.Calcd.,%: N 4.59; S 31.48.
.В аналогичных услови х с количественным выходом нолучают другие вещества.In similar conditions, other substances are obtained in quantitative yield.
Предмет изобретени Subject invention
1. Снособ получени (З-арилтиоэтиловых эфиров N-арилдитиокарбаминовых кислот общей формулы1. A process for the preparation of (N-arylthioethyl esters of N-aryldithiocarbamic acids of the general formula
2020
ЛпLp
лгын-с-3-сн,,-(;н,-йlgun-s-3-sn ,, - (; n, -th
2525
где Аг - незамещенный или замещенный фесоединений , (З-арилтиоэтилмеркаптаны подвергают взаимодействию с арилизотиоцианатами. 2 Способ по п , отличающийс тем, что процесс провод т в органических растворител х , например бензоле.5 3. Способ по пп. 1 и 2, отличающийс тем, что процесс провод т в присутствии каталитических количеств третичных основании, например триэтиламина, пиридина, при температуре 100-140°С.where Ar is unsubstituted or substituted with photo compounds, (3-arylthioethyl mercaptans are reacted with aryl isothiocyanates. 2 The method according to claim 4, wherein the process is carried out in organic solvents, for example benzene. 5 3. The method according to claims 1 and 2, characterized in that the process is carried out in the presence of catalytic amounts of tertiary bases, for example triethylamine, pyridine, at a temperature of 100-140 ° C.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU189874A1 true SU189874A1 (en) |
Family
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5037991A (en) * | 1984-07-18 | 1991-08-06 | Sandoz Ltd. | Novel substituted aromatic compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5037991A (en) * | 1984-07-18 | 1991-08-06 | Sandoz Ltd. | Novel substituted aromatic compounds |
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