Potassium Carbonate → 2-[p-(phenylthio)phenoxy]ethylthiocarbamic acid S-ethyl ester
Reaction equation
[C:1]1([S:7][C:8]2[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][NH2:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([S:20][C:21](Cl)=[O:22])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:18]([S:20][C:21](=[O:22])[NH:15][CH2:14][CH2:13][O:12][C:11]1[CH:16]=[CH:17][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[CH3:19]Participants
5
Procedure
7 g of 2-[p-(phenylthio)phenoxy]ethylamine and 18.6 g of chlorothioformic acid S-ethyl ester are dissolved in 250 ml of acetone. 24 g of potassium carbonate are added to the solution and the mixture is heated under reflux for 6 hours. The mixture is then filtered, the residue is washed with acetone and the filtrate is evaporated in vacuo. The 13 g of residue are filtered through a 10-fold amount of silica gel with ether/cyclohexane (7:3). The first fractions yielded 10.2 g which, after recrystallization from ether/low boiling petroleum ether yields 6.3 g (76%) of 2-[p-(phenylthio)phenoxy]ethylthiocarbamic acid S-ethyl ester, m.p.--77°-79° C.
Workup
- temperaturethe mixture is heated
- temperatureunder reflux for 6 hours
- filtrationThe mixture is then filtered
- washthe residue is washed with acetone
- customthe filtrate is evaporated in vacuo
- filtrationThe 13 g of residue are filtered through a 10-fold amount of silica gel with ether/cyclohexane (7:3)
- customThe first fractions yielded 10.2 g which
- customafter recrystallization from ether/low
Sources & evidence
- ORD record
- ord-0d9bfb391cb74699bfd4162923edab52
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215139
Reaction notes
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