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 2 M sodium carbonate and the aqueous layer acidified to pH 1 with 2 M 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 2 M 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-2edec92de56d402794cf7db2ab0d9daa
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656573
Reaction notes
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