Water → 4-Methylthio-3-nitrobenzoic acid

HRID 1385034Notes

Reaction equation

HRID 1385034 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 to 55-60° 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-5d20f4cd72164840b85c93e272fe6fff
Source dataset
uspto-grants-2001_07
Patent number
US06262074B1

Reaction notes

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