Potassium Nitrate → Methyl [3-(chlorosulfonyl)phenyl]acetate

HRID 491540

Reaction equation

HRID 491540 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

HCID 24434Potassium NitrateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 14820216Methyl 2-(3-mercaptophenyl)acetate

Product 1

HCID 23388821Methyl [3-(chlorosulfonyl)phenyl]acetateYield 79%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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 afford methyl 2-(3-chlorosulfonylphenyl)acetate as an oil (0.59 g, 2.4 mmol, 79% yield). 1H NMR (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

  1. temperaturethe reaction mixture was let warm to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-08aff3d6ddee47f89a330fbb070def5f
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Linked notes

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