Water → N-(1,3-thiazol-2-yl)-4-nitro-2-trichloromethylphenylsulfenamide

HRID 443774Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16]Cl)=[C:12]([C:18]([Cl:21])([Cl:20])[Cl:19])[CH:11]=1)([O-:9])=[O:8].O>O1CCCC1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][S:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][C:12]=1[C:18]([Cl:19])([Cl:20])[Cl:21]

Participants

Conditions

Temperature: 10 °C

Procedure

40 g of 2-aminothiazole is dissolved in 500 ml of tetrahydrofuran; while stirring and at 10° C., 61.4 g of 4-nitro-2-trichloromethylbenzenesulfenyl chloride is added. The addition of water precipitates the sulfenamide, which is filtered and recrystallized from ethyl acetate. There is obtained 50 g (70% of theory) of N-(1,3-thiazol-2-yl)-4-nitro-2-trichloromethylphenylsulfenamide; m.p.: 165° C.

Workup

customprecipitates the sulfenamide, which
filtrationis filtered
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-8639666210024c48959d2c2918f0497a
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04261924

Reaction notes

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