SU222372A1 - METHOD FOR PRODUCING N-CARBETOXYMETHYLKARBA- ETHER - Google Patents
METHOD FOR PRODUCING N-CARBETOXYMETHYLKARBA- ETHERInfo
- Publication number
- SU222372A1 SU222372A1 SU1136717A SU1136717A SU222372A1 SU 222372 A1 SU222372 A1 SU 222372A1 SU 1136717 A SU1136717 A SU 1136717A SU 1136717 A SU1136717 A SU 1136717A SU 222372 A1 SU222372 A1 SU 222372A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbetoxymethylkarba
- ether
- producing
- carbethoxymethylcarbamic
- acid
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTMJPALEWBKCAH-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)carbamic acid Chemical compound CCOC(=O)CNC(O)=O DTMJPALEWBKCAH-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IJJJSNBMFDDFBC-UHFFFAOYSA-N 2-cyanoethyl acetate Chemical compound CC(=O)OCCC#N IJJJSNBMFDDFBC-UHFFFAOYSA-N 0.000 description 1
- DTMJPALEWBKCAH-UHFFFAOYSA-M N-(2-ethoxy-2-oxoethyl)carbamate Chemical compound CCOC(=O)CNC([O-])=O DTMJPALEWBKCAH-UHFFFAOYSA-M 0.000 description 1
- MSTWLSWFJFLFKH-UHFFFAOYSA-N [N-]=C=O.CCOC(C)=O Chemical compound [N-]=C=O.CCOC(C)=O MSTWLSWFJFLFKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- -1 chlorophenyl ester Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Description
Изобретение относитс к области получени нафтильных и арильных эфиров N-карбэтоксиметилкарбаминовой кислоты, содержащих в феиильном и нафтильном радикале ,различные заместители.This invention relates to the field of preparing naphthyl and aryl esters of N-carbethoxymethylcarbamic acid, containing various substituents in the feiil and naphthyl radical.
Вышеупом нутые зфиры могут найти применение в качестве физиологически активных веществ.The above-mentioned zephras can be used as physiologically active substances.
ЭфИ|ры N-карбэтоксиметилкарбаМиновой кислоты получают взаимодействием изоцианатэтилацетата с замещенными фенолами или нафтолами в безводном органическом растворителе в присутствии каталитических количеств триэтиламина.N-carbethoxymethylcarbamic acid esters are obtained by reacting isocyanateethyl acetate with substituted phenols or naphthols in an anhydrous organic solvent in the presence of catalytic amounts of triethylamine.
Пример. К раствору 3,9 г (0,02 моль) /г-хлорфенола в безводном бензоле (или другом безводном подход щем растворителе) в присутствии каталитических количеств триэтиламина добавл ют при перемешивании при комнатной температуре бензольный ipacTBOp 3,9 г (0,02 моль) цианатэтилацетата. Реакци протекает с небольщим разогреванием. Реакционную смесь выдерживают при перемешивании около 1 час, затем растворитель отгон ют , а остаток очищают перекристаллизацией из смеси бензола с петролейным эфиром. Точка плавлени «,-хлорфенилового эфира N-карбэтоксиметилкарбаминовойкислотыExample. To a solution of 3.9 g (0.02 mol) / g-chlorophenol in anhydrous benzene (or another anhydrous suitable solvent) in the presence of catalytic amounts of triethylamine, benzene ipacTBOp 3.9 g (0.02 mol a) cyanoethyl acetate. The reaction proceeds with a slight warming. The reaction mixture is kept under stirring for about 1 hour, then the solvent is distilled off, and the residue is purified by recrystallization from a mixture of benzene and petroleum ether. Melting point of "N-carbethoxymethylcarbamic acid chlorophenyl ester
35-36°С. Выход 80% от теоретического.35-36 ° C. Output 80% of theoretical.
Найдено, %: N 5,15, 5,10.Found,%: N 5,15, 5,10.
Вычислено, %: N 5,45.Calculated,%: N 5.45.
Свойства аналогично полученных соединений Ы-карбэтоксиметилкарбаматов приведепы в таблице.Properties similar to the obtained compounds of N-carbethoxymethylcarbamate are given in the table.
Предмет изобретени Subject invention
Способ получени эфиров N-карбэтоксиметилкарбаминовой кислоты, отличающийс тем, что изоцианатэтилацетат подвергают взаимодействию с замещенными фенолами или нафтолами в безводном органическом растворителе в присутствии каталитических количеств триэтиламина. Свойства эфироз N-карбэтоксиметилкарбаминовой кислоты 222372 Таблица С2Н500ССН2 N HCOORA process for the preparation of N-carbethoxymethylcarbamic acid esters, characterized in that the isocyanate-ethyl acetate is reacted with substituted phenols or naphthols in an anhydrous organic solvent in the presence of catalytic amounts of triethylamine. Properties of esterosis N-carbethoxymethylcarbamic acid 222372 Table С2Н500ССН2 N HCOOR
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU222372A1 true SU222372A1 (en) |
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