Benzyl mercaptan → Methyl 2-benzylthio-3-methylbenzoate

HRID 466744

Reaction equation

HRID 466744 reaction equation
[N+]([C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O.[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:15]([S:22][C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 19814653Methyl 2-benzylthio-3-methylbenzoateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 5 1 pot was charged 483 g of methyl 2-nitro-3-methylbenzoate, 319 g benzyl mercaptan and 100 mL dimethyl formamide. Upon cooling to 0° C., a solution of 321 g potassium tert-butoxide in 1500 mL dimethyl formamide was added dropwise over 2.5 hours at 0°-5° C. The reaction mixture was stirred at 0° C. for 1.5 hours and then at room temperature overnight. The reaction was quenched by addition of 1 1 water and worked up by extraction with 2 1 methylene chloride. Upon washing with water (3×1 1), the methylene chloride layer was dried over MgSO4, filtered and rotovapped to give 517 g of crude methyl 2-benzylthio-3-methylbenzoate (77% yield) as a liquid.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction was quenched by addition of 1 1 water
  4. extractionworked up by extraction with 2 1 methylene chloride
  5. washUpon washing with water (3×1 1)
  6. dry with materialthe methylene chloride layer was dried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-251b926d3d2049a88b3614d57d58e3ff
Source dataset
uspto-grants-1992_10
Patent number
US05157119

Linked notes

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