[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([Cl:13])[C:9]=1[O:10][CH2:11][CH3:12])[NH2:6])[CH3:2].CCN(C1C=CC=CC=1)CC.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][C:26](=[O:27])[O:28][CH:29]([CH3:31])[CH3:30])[CH:7]=[C:8]([Cl:13])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]3-Ethyl-4-ethoxy-5-chloroaniline (1.9 g) and diethylaniline (1.5 g) were dissolved in toluene (20 ml). To the resultant solution was dropwise added isopropyl chloroformate (1.2 g) in 5 minutes under ice-cooling. After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene as the eluent to give isopropyl N-(3-ethyl-4-ethoxy-5-chlorophenyl)carbamate (Compound No. 53) (2.4 g) in a yield of 89%. M.P., 79°-80.5° C.
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