Hydrochloric Acid → 2-(Methylthio)-5-nitrobenzoic acid

HRID 637107Notes

Reaction equation

HRID 637107 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][S-:15].[Na+].Cl>CO>[CH3:14][S:15][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 4378561Sodium methanethiolate

Product 1

HCID 234999612-(Methylthio)-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-fluoro-5-nitrobenzoic acid (prepared by the method of Tetrahedron, 23, 4041-4045 (1967)) (3.7 g, 20 mmol) and sodium thiomethoxide (2.8 g, 40 mmol) in methanol (60 mL). Heat to reflux. After 24 hours, cool the reaction mixture, adjust the pH to about 2 using aqueous 1 M hydrochloric acid solution. Extract the reaction mixture with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 2-methylthio-5-nitrobenzoic acid: Rf=0.5 (silica gel, 10% methanol/dichloromethane).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool the reaction mixture
  3. extractionExtract the reaction mixture with ethyl acetate
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-f15dd472f21e4573bbf3bae4f466b414
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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