N,N-Diethylaniline → 5-Acetyl-2-methylbenzene-1-sulfonamide
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:14])=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2].C([N:17](CC)C1C=CC=CC=1)C.C(C1C=CC(C)=C(S([O-])(=O)=O)C=1)(=O)C>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:14])=[C:8]([S:10]([NH2:17])(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2]Participants
4
Procedure
Thus obtained 5-acetyl-2-methylbenzenesulfonyl chloride was dissolved in 790 g of tetrahydrofuran, then 81 g of ammonia gas was added at a temperature below 10° C. 800 Grams of water was added to this reaction mixture, and tetrahydrofuran was removed by evaporation to crystallized 5-acetyl-2-methylbenzenesulfonamide. The crystals were collected by filtration, and dried to obtain 176.8 g (0.83M) of 5-acetyl-2-methylmethylbenzenesulfonamide. Melting point: 150.5°-151.5° C. The yield was 95% on the basis of 5-acetyl-2-methylbenzenesulfonyl chloride, and was 83% on the basis of N,N-diethylaniline salt of 5-acetyl-2-methylbenzenesulfonate.
Sources & evidence
- ORD record
- ord-e23c13f9a8c54b40aba8bccacff2e058
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04943655
Reaction notes
Loading…