SU201376A1 - METHOD OF OBTAINING O-ALKYL-O- (B-ARYLTIOETHYL) -CARBONATES - Google Patents
METHOD OF OBTAINING O-ALKYL-O- (B-ARYLTIOETHYL) -CARBONATESInfo
- Publication number
- SU201376A1 SU201376A1 SU1077300A SU1077300A SU201376A1 SU 201376 A1 SU201376 A1 SU 201376A1 SU 1077300 A SU1077300 A SU 1077300A SU 1077300 A SU1077300 A SU 1077300A SU 201376 A1 SU201376 A1 SU 201376A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- carbonates
- obtaining
- aryltioethyl
- ethyl
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic Effects 0.000 description 2
- -1 heterocyclic amines Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
Предметом насто щего изобретени вл етс способ получени неописанных в литературе О-алкил-О- (р-арилтиоэтил)-карбонатов общей формулы ArSCH2CH2OCOOR, где Аг - замещенный или незамещенный фенил; R - алкил, реакцией р - арилтиоэтанолов с хлоркарбоната.ми при 70-80°С в присутствии каталитических количеств гетероциклических аминов, например пиридина.The subject of the present invention is a process for the preparation of O-alkyl-O- (p-arylthioethyl) carbonates of the general formula ArSCH2CH2OCOOR, which are not described in the literature, where Ar is a substituted or unsubstituted phenyl; R is alkyl, by reaction of p-arylthioethanols with chlorocarbonate at 70-80 ° C in the presence of catalytic amounts of heterocyclic amines, for example pyridine.
Процесс ведут в органических растворител х (например бензоле) или без них.The process is carried out in organic solvents (for example, benzene) or without them.
Пример 1. О-этил-О-(р-фенилтиоэтил)карбонат .Example 1. O-ethyl-O- (p-phenylthioethyl) carbonate.
Смесь 3,9 г (0,025 г-люль) р-фенилтиоэтаиола , 2,7 г (0,025 г-моль этилхлорформиата, 7 мл бензола и 0,01 г пиридина кип т т в приборе с обратным холодильником до прекращени выделени хлористого водорода. Конечный продукт выдел ют ректификацией. Получают 5,4 г (95о/о) вещества; т. кип. 138- (1,5 мм}; 1,1424; п 1,5330; MRs 61,40, выч. 61,89.A mixture of 3.9 g (0.025 g-lul) of p-phenylthioethiol, 2.7 g (0.025 g-mol of ethyl chloroformate, 7 ml of benzene and 0.01 g of pyridine is boiled under reflux until the evolution of hydrogen chloride stops. the product is isolated by rectification. 5.4 g (95 ° / o) of the substance are obtained: bp 138- (1.5 mm}; 1.1424; p 1.5330; MRs 61.40, calc. 61.89.
Найдено, о/о: S 14,01.Found, o / o: S 14.01.
С11П140з5S11P140z5
(0,7 (0.7
1,1772; ng 1,5362; MRg 67,82, выч. 68,16.1.1772; ng 1.5362; MRg 67.82, calc. 68.16.
Пайдено, о/о: S 12,74.Paideno, o / o: S 12.74.
CioHioOiSCioHioOiS
Вычислено, %: S 12,50.Calculated,%: S 12.50.
Пример 3. О-этил-О- р- (о-метоксифенилтио )-этил -карбонат получен в услови х приЛ1ера 1 с выходом 92о/о- Т. кип. 164-165°С (1,5 мм}; d2° 1,1887; п 1,5430; MRg 67,89;Example 3. O-ethyl-O-p- (o-methoxyphenylthio) -ethyl carbonate was prepared under conditions of liter 1 with a yield of 92 ° / o- T. bale. 164-165 ° C (1.5 mm}; d2 ° 1.1887; p 1.5430; MRg 67.89;
выч. 68,16.Calc 68.16.
Найдено, о/о: S 12,36.Found, o / o: S 12.36.
Ci2ni(j04SCi2ni (j04S
Вычислено, %: S 12,50.Calculated,%: S 12.50.
Пример 4. О-этил-О- ip- (г-хлорфенилтио )-этил -карбонат получен в услови х примера 1 с выходом 960/0. Т. кип. 138-140°С (0,9 мм}; 1,2451; nfo 1,5469; MRg 66,34; выч. 66,76.Example 4. O-ethyl-O-ip- (g-chlorophenylthio) -ethyl carbonate was prepared under the conditions of Example 1 in 960/0 yield. T. Kip. 138-140 ° C (0.9 mm}; 1.2451; nfo 1.5469; MRg 66.34; calc. 66.76.
Найдено, %: 12,54; 13,50.Found,%: 12.54; 13.50.
Вычислено, о/о: 12,28; 13,62.Calculated, o / o: 12.28; 13.62.
Пример 5. О-этил-О- р-(л-толилтио)этил -карбонат получен в услови х примера 1 с выходом 960/0. Т. кип. 142-144°С (1 мм}; d20 1,1083; ng 1,5320; MRg 67,09; выч. 66,51. 3 Предмет изобретени 1. Способ получени О-алкил-О-(|3-арилтиоэтил )-карбонатов общей формулы ArSCHsCHaOCOOR, где Аг -замещенный5 или незамещенный фенил; R - алкил, отличающийс тем, что р-арилтиоэтанолы подвер4 гают взаимодействию с хлоркарбонатами при 70-80°С в присутствии каталитических количеств гетероциклических аминов, например пиридина. 2. Способ по п. 1, отличающийс тем, что процесс ведут в органических растворител х, например бензоле.Example 5. O-ethyl-O-p- (l-tolylthio) ethyl carbonate was prepared under the conditions of example 1 with a yield of 960/0. T. Kip. 142-144 ° C (1 mm}; d20 1.1083; ng 1.5320; MRg 67.09; calc. 66.51. 3 Subject of the invention 1. Method of obtaining O-alkyl-O- (| 3-arylthioethyl) -carbonates of the general formula ArSCHsCHaOCOOR, where Arg is substituted 5 or unsubstituted phenyl; R is alkyl, characterized in that the p-arylthioethanols are reacted with chlorocarbonates at 70-80 ° C in the presence of catalytic amounts of heterocyclic amines, for example pyridine. Claim 1, characterized in that the process is carried out in organic solvents, for example benzene.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU201376A1 true SU201376A1 (en) |
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