Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10]C(C)(N)C)=[CH:4][CH:3]=1.C([N:17]([CH2:20][CH3:21])CC)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[CH2:32](Cl)Cl>>[C:26]1([O:25][C:23](=[O:24])[N:17]([CH2:10][CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:20]([CH3:21])[CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
Procedure
To a solution of 38.5 g (0.15 mole) of N-[2-(4-fluorophenylthio]ethyl-1-methyl-ethanamine and 15.5 g (0.15 mole) of triethylamine in 300 ml of methylene chloride which was cooled in an ice bath was added dropwise with stirring a solution of 23.5 g (0.15 mole) of phenyl chloroformate in 100 ml of methylene chloride over a 15 minute period. The resulting solution was stirred overnight at room temperature and extracted with 5% aqueous sodium hydroxide. The chloroform layer was dried and filtered and evaporated to give an oil residue which crystallized to a white solid. A portion of the solid was triturated with isopropyl ether and the mixture cooled under refrigeration. The solid was collected by filtration and dried in vacuo overnight at 80° C. White crystalline product, m.p. 53°-58° C. was obtained.
Workup
- additionwas added dropwise
- extractionextracted with 5% aqueous sodium hydroxide
- dry with materialThe chloroform layer was dried
- filtrationfiltered
- customevaporated
- customto give an oil residue which
- customcrystallized to a white solid
- customA portion of the solid was triturated with isopropyl ether
- temperaturethe mixture cooled under refrigeration
- filtrationThe solid was collected by filtration
- customdried in vacuo overnight at 80° C
- customWhite crystalline product, m.p. 53°-58° C. was obtained
Sources & evidence
- ORD record
- ord-d538191b40094b7b8b9056315b257523
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04597902
Linked notes
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