Diisopropylethylamine → N-[2-(4-chlorophenyl)-2-oxoethyl]-N'-cyclopropylurea

HRID 660864Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[CH:13]1([N:16]=[C:17]=[O:18])[CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:3][NH:2][C:17]([NH:16][CH:13]2[CH2:15][CH2:14]2)=[O:18])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1000 mg (4.853 mmol) of 2-amino-1-(4-chlorophenyl)ethanone hydrochloride are placed in 20 ml dichloromethane, cooled to 0° C. and treated dropwise with a solution of 363 mg (4.367 mmol) of cyclopropyl isocyanate in 2 ml dichloromethane. It is stirred a further 10 mins at 0° C. and then a solution of 627 mg (4.853 mmol) of N,N-diisopropylethylamine in 4 ml dichloromethane is added dropwise. After two hours' stirring at room temperature the reaction mixture is evaporated and the crude product purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 100:1). 1000 mg (73% of theory) of the target compound are obtained.

Workup

stirringAfter two hours' stirring at room temperature the reaction mixture
customis evaporated
customthe crude product purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 100:1)
custom1000 mg (73% of theory) of the target compound are obtained

Sources & evidence

ORD record: ord-898df1a07a834e19b27ce607529c941f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084481B2

Reaction notes

Loading…