Reaction #904

Reaction equation

ammonia

water

2-methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride

→

4-Methyl-5-nitrosaccharin

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Concentrationthe mixture is concentrated on a rotary evaporator
2. 2
   Otherto remove water and THF
3. 3
   workup.STIRRINGThe residue which remains is stirred with ethyl acetate
4. 4
   Filtrationfiltered off with suction
5. 5
   Washwashed with ethyl acetate
6. 6
   OtherAfter drying under reduced pressure, 34 g (0.131 mol)=79% of theory of a white solid of m.p.: 312° C. (dec.)
7. 7
   Otherare obtained

Procedure

104 ml of 25% ammonia solution are initially taken, 100 ml of water are added and a solution of 48.7 g (0.166 mol) of 2-methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride in 70 ml of tetrahydrofuran is then added dropwise at 10° C. After stirring at 25° C. for three hours, the mixture is concentrated on a rotary evaporator to remove water and THF. The residue which remains is stirred with ethyl acetate, filtered off with suction and washed with ethyl acetate. After drying under reduced pressure, 34 g (0.131 mol)=79% of theory of a white solid of m.p.: 312° C. (dec.) are obtained.

Source