[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([NH:6][CH2:7][C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])=[C:10](OC)[CH:9]=2)=[CH:4][CH:3]=1.C(S)C.[H-].[Na+]>CN(C)C=O>[CH3:20][C:13]1([CH3:19])[C:14](=[O:16])[O:15][C:21]2[CH:22]=[C:8]([CH2:7][NH:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=3)[CH:9]=[CH:10][C:11]=2[O:12]1A mixture of 500 mg of ethyl 2-[4-(4-chloroanilinomethyl)-2-methoxyphenoxy]-2-methylpropionate, 206 mg of ethanethiol, 159 mg of 50% sodium hydride and 10 ml of dimethylformamide is heated at 100° C. for 3 hours. The reaction mixture is poured into ice-water and washed with ether. The aqueous layer is adjusted to pH 2 with 10% hydrochloric acid and extracted with ether. The extract is washed with water, dried and concentrated. The residue is pulverized with a mixture of diisopropyl ether and n-hexane and the crystals are collected by filtration to give 250 mg of 3,3-dimethyl-7-(4-chloroanilinomethyl)-1,4-benzodioxan-2-one, mp 97° to 98° C. From the mother liquor 60 mg of the same compound is further obtained.
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