Water → 4-Methylthio-3-nitrobenzoic acid

HRID 1017124Notes

Reaction equation

HRID 1017124 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C[O-].[Na+].[CH3:17][S-:18].[Na+].O>CO>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[S:18][CH3:17])[C:6]([OH:8])=[O:7])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 679874-Fluoro-3-nitrobenzoic acidHCID 4378561Sodium methanethiolateHCID 10942334Sodium Methoxide

Product 1

HCID 5425314-Methylthio-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
57.5 °C

Procedure

0.75 mol of 4-fluoro-3-nitrobenzoic acid was charged in 2 l of methanol, and 0.75 mol of sodium methoxide was added dropwise. 0.83 mol of sodium thiomethoxide was then added and the reaction mixture was heated at from 55 to 60° C. for 5 hours. After cooling, 1 l of water was added, the precipitate was filtered off with suction and washed with 100 ml of methylene chloride. The residue was then taken up in 500 ml of 2 N hydrochloric acid and the precipitate formed was filtered off with suction and washed with water. The residue was then taken up in tetrahydrofuran and dried over sodium sulfate and the solvent was distilled off.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with 100 ml of methylene chloride
  4. customthe precipitate formed
  5. filtrationwas filtered off with suction
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-f985cc9ac96c4c3585c6216d8ba41370
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Reaction notes

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