Reacción #40789

Ecuación de reacción

methyl chloroformate

2-chloro-benzenesulfonamide

triethylamine

→

white solid

(2-Chloro-benzenesulfonyl)-carbamic acid methyl ester

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled with an ice bath
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.ADDITIONWater was added and de aqueous layer
4. 4
   Lavadowas washed two times with ether
5. 5
   FiltraciónThe suspension was filtered
6. 6
   Lavadothe residue was washed with H2O
7. 7
   Otrodried in vacuo

Procedimiento

To 25.0 g 2-chloro-benzenesulfonamide was added 75 mL acetonitrile and 45.2 mL (2.5 eq) triethylamine. The mixture was cooled with an ice bath and 15.1 mL methyl chloroformate was slowly added dropwise. The mixture was stirred overnight at room temperature and concentrated in vacuo. Water was added and de aqueous layer was washed two times with ether. Acidification of the aqueous layer with 2 M HCl led to formation of a white precipitate. The suspension was filtered, the residue was washed with H2O and dried in vacuo to yield 19.1 g of a white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.58 (s, 3H), 7.52-7.61 (m, 1H), 7.62-7.72 (m, 2H), 8.10 (dd, J=8 and 1.5 Hz, 1H), 12.42 (br s, 1H).

Fuente