2-amino-5-chlorobenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 2-amino-5-chlorobenzenesulfonamide and cyclopropylmethyl isothiocyanate by a method analogous to the one described in Example 4; m.p. 288-290° C. (ethyl acetate); 1H-NMR (DMSO-d6): δ 0.20-0.54 (m, 4H, CH2CH2), 1.05 (m, 1H, CH), 3.10 (distorted t, 1H, NHCH2), 7.22 (d, 1H, ArH), 7.31 (br., 1H, NH), 7.55-7.69 (m, 2H, ArH), 10.7 (br.s, 1H, NH); MS: m/e 285/287 (M+); (C11H12N3Cl1O2S1) calc. C, 46.24; H, 4.23; N, 14.71; found C, 46.48; H, 4.32; N, 14.72.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 2-amino-5-chlorobenzenesulfonamide and cyclopropylmethyl isothiocyanate by a method analogous to the one described in Example 4; m.p. 288-290° C. (ethyl acetate); 1H-NMR (DMSO-d6): δ 0.20-0.54 (m, 4H, CH2CH2), 1.05 (m, 1H, CH), 3.10 (distorted t, 1H, NHCH2), 7.22 (d, 1H, ArH), 7.31 (br., 1H, NH), 7.55-7.69 (m, 2H, ArH), 10.7 (br.s, 1H, NH); MS: m/e 285/287 (M+); (C11H12N3Cl1O2S1) calc. C, 46.24; H, 4.23; N, 14.71; found C, 46.48; H, 4.32; N, 14.72.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1 g of 2-amino-5-chlorobenzenesulphonamide (obtained in accordance with J. Chem. Soc. Perkin I 1979, 1043-1047) dissolved in 4 ml of dioxane there are added, in the cold state (+5° C.), 0.6 ml of pyridine and 0.6 ml of difluoroacetic acid chloride. The flask is hermetically closed immediately and subjected to vigorous stirring at ambient temperature for 10 minutes. The solvents are then removed under reduced pressure. The solid residue is taken up in water (12 ml), and the insoluble material is collected by filtration, washed with water and dried to yield the expected compound. The flask is hermetically closed immediately The solvents are then removed under reduced pressure the insoluble material is collected by filtration washed with water dried

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40 ml of ethyl orthoformate are added to 4.75 g of 2-amino-5-chlorobenzenesulphonamide, the preparation of which is described in the journal J. Chem. Soc. Perkin I 1979, 1043-1047. The mixture is heated at 110° C. for 30 minutes in an open vessel. Dissolution is observed, and then the appearance of a precipitate. the preparation of which Dissolution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-chlorobenzenesulfonamide (8.0 g., 0.039 mole) and 4-(2-dimethylaminoethyl)cyclohexanone (13.5 g., 0.08 mole) in 0.6 N ethanolic HCl (110 ml.) is heated at reflux 18 hours. The solvent is evaporated at reduced pressure and the residue dissolved in water (100 ml.) and neutralized with sodium hydroxide to precipitate 4'-(2-dimethylaminoethyl)-7-chlorospiro-[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide hemisemihydrate which melts at 234°-5° C. after recrystallization from n-propanol. is heated at reflux 18 hours The solvent is evaporated at reduced pressure the residue dissolved in water (100 ml.) to precipitate 4'-(2-dimethylaminoethyl)-7-chlorospiro-[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide hemisemihydrate which melts at 234°-5° C. after recrystallization from n-propanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-chlorobenzenesulphonamide (obtained according to J. Chem. Soc. Perkin I, 1043-1047, 1979) and ethyl orthoformate (40 mL) is heated at boiling for 30 minutes in an open vessel. The volume of the mixture is reduced by half under reduced pressure. The precipitate obtained is collected by filtration, washed with ether and dried. is heated The precipitate obtained is collected by filtration washed with ether dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-chlorobenzenesulphonamide (obtained according to J. Chem. Soc. Perkin I, 1043-1047, 1979) and ethyl orthoformate (40 mL) is heated at boiling for 30 minutes in an open vessel. The volume of the mixture is reduced by half under reduced pressure. The precipitate obtained is collected by filtration, washed with ether and dried. is heated The precipitate obtained is collected by filtration washed with ether dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized as described for Example 194 a) in 49% yield, starting from 2-amino-5-chlorobenzenesulfonamide and (E)-2-(3,4-dichlorophenyl)ethenesulfonyl chloride (1.5 equiv.). Purification by column chromatography, using chloroform/methanol (95:5) as the eluent. Purification by column chromatography