Acetic Acid → 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzoic acid
Reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10](N)=[O:11])=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1)(=[O:5])=[O:4].C(O)(=[O:22])C.S(=O)(=O)(O)O.N(OCCC(C)C)=O>O>[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:22])=[O:11])=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1)(=[O:5])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzamide (1.38 g), acetic acid (10 ml) and concentrated sulphuric acid (0.5 ml) were heated to 70° C. and isoamyl nitrite (15 ml) was added over 4 hours. After cooling the mixture was poured into water and extracted with ethyl acetate and washed with water. The organic phase was extracted with 2M sodium carbonate and the aqueous layer acidified to pH 1 with 2M HCl. This was extracted with ethyl acetate, washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue passed through a short silica column eluting with dichloromethane-ethyl acetate to give 4-(N,N-dimethylsulphamoyl)-2-trifluoromethylbenzoic acid (0.98 g) as a white solid, m.p. 188.8°-189.4° C.
Workup
- temperatureAfter cooling the mixture
- extractionextracted with ethyl acetate
- washwashed with water
- extractionThe organic phase was extracted with 2M sodium carbonate
- extractionThis was extracted with ethyl acetate
- washwashed with water
- dry with materialdried (anhydrous magnesium sulphate)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- washeluting with dichloromethane-ethyl acetate
Sources & evidence
- ORD record
- ord-351547cfd3ee4331ae8b6895b7236237
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859283
Reaction notes
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