Potassium Nitrate → Methyl [3-(chlorosulfonyl)phenyl]acetate
Reaction equation
S[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[N+]([O-])([O-])=O.[K+].[S:18]([Cl:22])(Cl)(=[O:20])=[O:19].C(=O)(O)[O-].[Na+]>C(#N)C.C(OCC)(=O)C>[Cl:22][S:18]([C:6]1[CH:5]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:3]=[CH:2][CH:7]=1)(=[O:20])=[O:19]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyl 2-(3-mercaptophenyl)acetate (0.55 g, 3.0 mmol) was dissolved in 10 mL acetonitrile and potassium nitrate (0.76 g, 7.5 mmol) was added and the reaction mixture cooled to 0° C. To this suspension sulfuryl chloride was added (0.6 mL, 7.5 mmol) at 0° C. and the reaction mixture was let warm to room temperature and stirred overnight. A solution of saturated sodium bicarbonate was added followed by ethyl acetate (100 mL each). The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil 0.59 g, 2.4 mmol, 79% yield. 1H NMR 500 MHz (CDCl3) 7.91 ppm, 2H, m; 7.60 ppm, 1H, d; 7.53 ppm, 1H, t; 3.73 ppm, 2H, s; 3.72 ppm, 3H, s.
Workup
- temperaturethe reaction mixture was let warm to room temperature
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-b6d0fbbd1b814aad8868f73c49b1aba8
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514448B2
Reaction notes
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