Reaction #51667

Reaction equation

N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-2,2,2-trifluoro-acetamide

sodium hydroxide

→

2-chloro-6-methanesulfonylmethyl-phenylamine

Yield 90.0%

Conditions

Workup

1. 1
   Temperatureheated in an oil bath
2. 2
   workup.STIRRINGThe homogeneous solution was stirred at this temperature for 90 minutes
3. 3
   Temperatureto cool to room temperature
4. 4
   OtherThe flask was immersed in an ice bath
5. 5
   workup.ADDITIONthe suspension of the product
6. 6
   workup.STIRRINGwas stirred at this temperature until all was crystalline
7. 7
   FiltrationFiltration
8. 8
   Washwashing well with water
9. 9
   Otherthorough drying

Procedure

The crystalline N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-2,2,2-trifluoro-acetamide of Step 3 was taken up into 200 ml of 2N solution of sodium hydroxide and stirred and heated in an oil bath heated to 120° C. The homogeneous solution was stirred at this temperature for 90 minutes and slowly allowed to cool to room temperature. The flask was immersed in an ice bath and the suspension of the product was stirred at this temperature until all was crystalline. Filtration, washing well with water and thorough drying afforded 13.96 g of pure crystalline 2-chloro-6-methanesulfonylmethyl-phenylamine (90%).

Source