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ChemicalBook CAS DataBase List CarbaMic acid, N-[(propylaMino)sulfonyl]-, 1,1-diMethylethyl ester
1393813-40-5

CarbaMic acid, N-[(propylaMino)sulfonyl]-, 1,1-diMethylethyl ester synthesis

2synthesis methods
-

Yield:1393813-40-5 97%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 2 h;

Steps:

General Procedure for the Preparation of Carboxylsulfonamide

General procedure: To the stirred solution of chlorosulfonyl isocyanate (CSI) (1.62 g, 1 mL, 11.48 mmol) in anhydrous methylene chloride (10 mL) at 0 °C was added tert-butanol (0.85 g, 1.09 mL, 11.48 mmol) in the same solvent (10 mL). After a period of 30 min, the resulting solution and triethylamine (1.75 mL, 1.1 equiv.) was slowly added to a solution containing primary amine (1 equiv.) in anhydrous methylene chloride (10 mL) at 0 °C. The resulting reaction solution was allowed to warm up to room temperature for over a period of 2 h. The reaction mixture was diluted with methylene chloride (30 mL) and washed with HCl 0.1 N (20 mL) and then with water (25 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to give carboxyl sulfonamides (1a-e) in excellent yields.

References:

Bouchareb, Fouzia;Boufas, Wahida;Cheloufi, Hadjer;Berredjem, Malika;Aouf, Nour-Eddine [Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,# 5,p. 587 - 595]