Acetyl chloride → HCID 21993065, compound

Participants

Reaction Steps

0.63 g (8 mmol) of acetyl chloride dissolved in 10 ml of dichloromethane is added dropwise to a solution, cooled to 0° C., of 2.01 g (6.7 mmol) of N-tert-butyl-5-amino-methyl-2-methoxycarbonylbenzenesulfonamide and 0.93 ml (6.7 mmol) of triethylamine in 30 ml of dichloromethane, and the mixture is then stirred at room temperature for 2 h. The reaction solution is washed with water, dried and evaporated to dryness i.v. 2.1 g (91%) of N-tert-butyl-5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide are obtained as a viscous oil.   1 ⁢ H ⁢   ⁢ NMR ⁢   ⁢ ( 100 ⁢   ⁢ MHz , CDCl 3 ) ⁢ : ⁢   ⁢ δ =   ⁢ 1.25 ⁢   ⁢ ( s , 9 ⁢ H , C ⁡ ( CH 3 ) 3 ) ,   ⁢ 2.05 ⁢   ⁢ ( s , 3 ⁢ H , COCH 3 ) ,   ⁢ 3.95 ⁢   ⁢ ( s , 3 ⁢ H , OCH 3 ) ,   ⁢ 4.50 ⁢   ⁢ ( s , 2 ⁢ H , Ar— ⁢ CH 2 ) ,   ⁢ 6.15 ⁢   ⁢ ( s , 1 ⁢ H , SO 2 ⁢ NH ) ,   ⁢ 6.38 ⁢   ⁢ ( bt , 1 ⁢ H , NH ) ,   ⁢ 7.47 ⁢   ⁢ ( dd , 1 ⁢ H , Ar ⁢ — ⁢ H ) ,   ⁢ 7.75 ⁢   ⁢ ( d , 1 ⁢ H , Ar ⁢ —H ) ,   ⁢ 7.95 ⁢   ⁢ ( dd , 1 ⁢ H , Ar ⁢ — ⁢ H ) .

Provenance & Evidence