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ChemicalBook CAS DataBase List 4-Isothiocyanatobenzene-1-sulfonamide

4-Isothiocyanatobenzene-1-sulfonamide synthesis

3synthesis methods
-

Yield: 87%

Reaction Conditions:

with calcium carbonate in dichloromethane;water at 0 - 20; under 760.051 Torr;Inert atmosphere;

Steps:

25 4-isothiocyanatobenzenesulfonamide
To a suspension of calcium carbonate (1.45 g, 14.5 mmol, Eq: 2.5) and thiophosgene (734 mg, 490 μ, 6.39 mmol, Eq: 1.1) in dichloromethane (13.2 g, 10 ml, 155 mmol, Eq: 26.8)/water (10.0 g, 10 ml, 555 mmol, Eq: 95.6) at 0, was added 4-aminobenzenesulfonamide (1 g, 5.81 mmol, Eq: 1.00). The reaction was gradually warmed to room temperature and stirred overnight. Added 15 mL IN HC1 slowly. Separated organic layer, and extracted the aqueous layer with ethyl acetate. Combined organic extracts were dried over sodium sulfate and concentrated to give 1.084 g (87%) of desired product as a white solid.

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;BILOTTA, Joseph Anthony;CHEN, Zhi;CHIN, Elbert;DING, Qingjie;ERICKSON, Shawn David;GABRIEL, Stephen Deems;KLUMPP, Klaus;MA, Han;MERTZ, Eric;PLANCHER, Jean-Marc;WEIKERT, Robert James WO2014/6066, 2014, A1 Location in patent:Paragraph 0211

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