Hydrochloric Acid → 4-Isothiocyanatobenzenesulfonamide

HRID 1820618Notes

Reaction equation

HRID 1820618 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[C:13](Cl)(Cl)=[S:14]>O>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][CH:3]=1)=[C:13]=[S:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5333SulfanilamideHCID 10040Thiophosgene

Product 1

HCID 5213594-Isothiocyanatobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-amino-benzenesulfonamide Compound 2a (40 g, 240 mmol) in water (400 mL) in the presence of concentrated hydrochloric acid (100 mL) was reacted with thiophosgene (26.8 g, 240 mmol) at r.t. for 30 mins to provide 4-isothiocyanato-benzenesulfonamide Compound 2b (85% yield) (procedure described in McKee R L and Bost R W, J. Am. Chem. Soc., 1946, 68, 2506-7).

Sources & evidence

ORD record
ord-cf77f28e8a994c5c84982bbe9f5cbd8f
Source dataset
uspto-grants-2009_10
Patent number
US07605154B2

Reaction notes

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