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

HRID 1066125Notes

Reaction equation

HRID 1066125 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:12])(=[O:11])[NH:9][C:8](=O)[NH:7][C:6]=2[CH:14]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[ClH:22].C(N(CC)CC)C>C(O)C>[NH:15]([C:8]1[NH:7][C:6]2[CH:14]=[CH:2][C:3]([Cl:22])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[N:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11130Triethylamine hydrochlorideHCID 124870946-chloro-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 211977853-Anilino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-015351dab00f4e64acd3d76d9fc4f5b5
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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