Water → Methyl 2-methyl-3-(sulfinylamino)benzoate

HRID 1639847Notes

Reaction equation

HRID 1639847 reaction equation
[S:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:7]([CH3:16])=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].O>C1C=CC=CC=1>[CH3:16][C:7]1[C:6]([N:5]=[S:1]=[O:2])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 38010253-Amino-2-methylbenzoic acid methyl ester

Product 1

HCID 12255793Methyl 2-methyl-3-(sulfinylamino)benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of thionyl chloride (6.63 mL, 91.0 mmol) in benzene (60 mL) was added a solution of methyl 3-amino-2-methylbenzoate (13.1 g, 91.0 mmol) in benzene (31 mL) at room temperature, and the mixture was heated under reflux for 18 hr. Water was added, and the mixture was extracted with dichloromethane, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (17.3 g, yield 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b80e2f519fb549e9a453cf86a820398f
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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