Water → N-methyl-N-methylthio-N'-(3,4-dichlorophenyl)-urea
Reaction equation
[CH3:1][S:2]Cl.C(OCC)C.[CH3:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=[O:12].O>N1C=CC=CC=1>[CH3:9][N:10]([S:2][CH3:1])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=[O:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
A mixture of 20 ml of methylsulfenyl chloride and 200ml of ethyl ether was added slowly while keeping the temperature below -30° C. to a solution of 40 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 500 ml of pyridine and the mixture was stirred for 1 hour at -30° C. After letting the temperature rise to 5° C., the mixture was stirred for 17 hours and the mixture was poured into a mixture of ice and water. The mixture was extracted with methylene chloride and the methylene chloride extract was washed with water and dried. The volatile fractions were removed by distillation under reduced pressure and the residue was crystallized from isopropyl ether to obtain 29.4 g of N-methyl-N-methylthio-N'-(3,4-dichlorophenyl)-urea melting at 93° C. A microanalytical sample was obtained by chromatography over silica gel and elution with a 9-1 benzene-ethyl acetate mixture.
Workup
- additionwas added slowly
- customthe temperature below -30° C.
- customto 5° C.
- stirringthe mixture was stirred for 17 hours
- extractionThe mixture was extracted with methylene chloride
- extractionthe methylene chloride extract
- washwas washed with water
- customdried
- customThe volatile fractions were removed by distillation under reduced pressure
- customthe residue was crystallized from isopropyl ether
Sources & evidence
- ORD record
- ord-1039c6c240cd4c9db0d30ab1815fd8bd
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04045209
Reaction notes
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