Benzyl mercaptan → HCID 54046874, compound

HRID 1639840Notes

Reaction equation

HRID 1639840 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.O>[CH2:21]([S:28][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 54046874HCID 54046874, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under nitrogen atmosphere, to a mixture of methyl 2-chloro-3-nitrobenzoate (20.8 g, 96.5 mmol) and potassium carbonate (40.0 g, 289 mmol) in N,N-dimethylformamide (300 mL) was added benzyl mercaptan (11.5 mL, 98.0 mmol) at 0° C., and the mixture was stirred at 90° C. for 6 hr, diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→1/2) to give the title compound (28.5 g, yield 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→1/2)

Sources & evidence

ORD record
ord-90a578dd3f1b4c3897d54bcde1997771
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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