Sodium hydrosulfide → Methyl 4-mercapto-2-methyl-5-nitrobenzoate

HRID 1942491Notes

Reaction equation

HRID 1942491 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[SH-:16].[Na+]>CO>[SH:16][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 10633188Methyl 4-chloro-2-methyl-5-nitrobenzoate

Product 1

HCID 58376194Methyl 4-mercapto-2-methyl-5-nitrobenzoateYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-chloro-2-methyl-5-nitrobenzoate (1.21 g) in methanol (20 ml) was added sodium hydrosulfide (561 mg), and the mixture was refluxed with stirring for 2 hours. After the reaction was complete, the reaction solution was concentrated, and methanol was concentrated under reduced pressure. Then, to the resultant were added water and 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (1.17 g).

Workup

  1. temperaturethe mixture was refluxed
  2. concentrationthe reaction solution was concentrated
  3. concentrationmethanol was concentrated under reduced pressure
  4. additionThen, to the resultant were added water and 2N hydrochloric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-4e30d340965041deb32d163a4d305239
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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