[OH-].[K+].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1)[CH3:4].[N+:16]([C:19]1[CH:25]=[CH:24][C:23](Cl)=[CH:22][C:20]=1[NH2:21])([O-:18])=[O:17]>O.CN(C)C=O>[N+:16]([C:19]1[CH:25]=[CH:24][C:23]([S:13][C:11]2[S:12][C:8]3[CH:7]=[C:6]([O:5][CH2:3][CH3:4])[CH:15]=[CH:14][C:9]=3[N:10]=2)=[CH:22][C:20]=1[NH2:21])([O-:18])=[O:17]To a stirred solution of 0.15 moles of potassium hydroxide in a mixture of 15 ml of water and 300 ml of dimethylformamide add 0.15 moles of 6-ethoxybenzothiazole-2-thiol (L. B. Sebrell and C. E. Boord, J. Am. Chem. Soc., 45, 2390 (1923)) under a nitrogen atmosphere. After complete dissolution, add 2-nitro-5-chloroaniline (R. C. Fuson, R. A. Dauman, E. Howard, Jr., and E. N. Marvell, J. Org. Chem., 12, 084 (1947)) and heat the mixture under reflux and a positive nitrogen pressure for about 16 hours. Pour the mixture into 1000 ml of water and remove the resulting precipitate. Wash the precipitate with water and crystallize from acetonitrile to give the title compound having a melting point of 126°-129° C.
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