B(Cl)(Cl)[Cl:2].Cl[CH2:6][C:7]1C=CC(N)=CC=1.[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18].C([N:27]([CH2:32]CCC)[CH2:28][CH2:29][CH2:30][CH3:31])CCC>C1C=CC=CC=1.CCOCC.O>[CH3:32][NH:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:2])=[CH:7][C:6]=1[CH:17]([OH:18])[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[Cl:14]
To a solution of boron trichloride (100 mg) in dry benzene (5 ml), a solution of p-chloromethylaniline (100 mg) in dry benzene (2 ml) is added with cold water cooling (7°-10° C.), and the resultant mixture is refluxed for 2 hours. Then, a solution of o-chlorobenzaldehyde (99 mg) and tri-n-butylamine (131 mg) in dry benzene (2 ml) is added thereto with cold water cooling, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with ether. The ethereal layer is washed with aqueous sodium carbonate and a saturated brine in that order, dried over potassium carbonate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylamino-5,2'-dichlorobenzhydrol (174 mg) as crystals melting at 106° to 108° C. The yield is 87.4%.
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