Aniline → 3-Anilino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide

Participants

Reaction Steps

The title compound was prepared from 6-chloro-2,3-dihydro-3-oxo-1,2,4-benzothiadiazine 1,1-dioxide (3.0 g, 12.9 mmol) and aniline (4.8 g, 52.0 mmol) by a method analogous to the method described in example 37, except that triethylamine hydrochloride (7.1 g, 52.0 mmol) was used instead of N,N-dimethylcyclohexylamine. Yield 1.68 g (44%) of pure product; m.p. (DSC) >350° C. (ethanol); 1H-NMR (DMSO-d6): δ 7.1-7.8 (m, 8H, ArH), 9.5 (br.s, 1H, NH), 11.05 (br.s, 1H, NH,; MS: m/e 307/309 (M+); (C13H10N3Cl1O2S1) calc. C, 50.74; H, 3.28; N, 13.65; found C, 50.31; H, 3.24; N, 13.59.

Provenance & Evidence