Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:18]=[C:17]([CH3:19])[C:15]([NH2:16])=[C:14]([CH3:20])[CH:13]=1.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1.O>[C:5]1([O:4][C:2](=[O:3])[NH:16][C:15]2[C:17]([CH3:19])=[CH:18][C:12]([Cl:11])=[CH:13][C:14]=2[CH3:20])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1A solution of 2.56 g of phenyl chloroformate in 20 ml of toluene was added to a cold solution of 2.47 g of 4-chloro-2,6-dimethylaniline and 2.4 ml of N,N-dimethylaniline in 80 ml of toluene. The resulting mixture was stirred at room temperature for 11/2 hours and then diluted with water The organic layer was washed with 3N hydrochloric acid, brine, dried, and evaporated. The residual solid was crystallized from ethylacetate:hexane to yield phenyl-N-(4-chloro-2,6-dimethylphenyl)carbamate, mp 158°-160° C.
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