Water → Methyl 2-(methylsulfanyl)-5-nitrobenzoate

HRID 2085484Notes

Reaction equation

HRID 2085484 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:15][SH:16].[Na].O>CN(C)C=O>[CH3:15][S:16][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 22754Methyl 2-chloro-5-nitrobenzoateHCID 45051789Methylmercaptan sodium

Product 1

HCID 7164673Methyl 2-(methylsulfanyl)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.02 g of methyl 2-chloro-5-nitrobenzoate dissolved in 100 ml of N,N-dimethylformamide, was added 23.92 g of a 15% aqueous solution of sodium methylmercaptan dropwise under ice cooling. The mixture was stirred for 30 minutes. Water was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over anhydrous magnesium sulfate. The crude product obtained by removal of the solvent under reduced pressure was recrystallized from ethyl acetate—hexane, to yield 8.76 g of methyl 2-methylthio-5-nitrobenzoate (melting point: 126.5-127.5° C.) (Reaction Scheme (42) described below).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe crude product obtained by removal of the solvent under reduced pressure
  5. customwas recrystallized from ethyl acetate—hexane

Sources & evidence

ORD record
ord-7c394b293d554786a5fa077650bfbf66
Source dataset
uspto-grants-2004_04
Patent number
US06720424B1

Reaction notes

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