2-BENZOTHIAZOLESULFONAMIDE, 6-NITRO- → Aminozolamide

HRID 1110371Notes

Reaction equation

HRID 1110371 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([C:14]1[CH:26]=[CH:25][C:17]2[N:18]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:20][C:16]=2[CH:15]=1)([O-:13])=[O:12]>S(=O)(=O)(O)O>[NH2:11][C:14]1[CH:26]=[CH:25][C:17]2[N:18]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:20][C:16]=2[CH:15]=1.[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([SH:1])[S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 133934272-BENZOTHIAZOLESULFONAMIDE, 6-NITRO-HCID 178418395HCID 178418395, compound2×

Product 2

HCID 93505AminozolamideYield 90%HCID 178418579HCID 178418579, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The title compound is prepared by first converting 2-mercaptobenzothiazole to 6-nitro-2-benzothiazolesulfonamide and then reducing to the 6-amino analog. 2-Mercaptobenzothiazole was converted to 2,2'-bis-benzothiazole disulfide in 90% yield: m.p. 175-177° C. Nitration in concentrated sulfuric acid gave 6-nitro-2-mercaptobenzothiazole in 59%. m.p. 255-258° C. The sulfenamide was formed by reaction with aqueous sodium hydroxide and sodium hypochlorite and oxidized in the next step without further purification. The oxidation was accomplished by dissolving the sulfenamide in dimethoxyethane, cooling the solution to -5° C., adding the m-chloroperoxybenzoic acid in dimethoxyethane and working up the reaction in the standard manner to obtain a 70% yield: m.p. 179-180°; MS, m/e 259 (M, calcd. 259). Anal. (C7H5N3O4S2) CHN.

Sources & evidence

ORD record
ord-63436b3e26e54ff1b074e88034b10993
Source dataset
uspto-grants-1990_12
Patent number
US04975448

Reaction notes

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