Hydrochloric Acid → 4-Dimethylthiocarbamoyloxy-3-fluoro-5-nitro-2-o-tolylamino-benzoic acid methyl ester

HRID 1795890Notes

Reaction equation

HRID 1795890 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][C:14](=[S:18])[N:15]([CH3:17])[CH3:16])=[C:6]([F:19])[C:5]=1F.Cl.[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][C:14](=[S:18])[N:15]([CH3:17])[CH3:16])=[C:6]([F:19])[C:5]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7242O-ToluidineHCID 542334314-Dimethylthiocarbamoyloxy-2,3-difluoro-5-nitrobenzoic acid methyl ester

Product 1

HCID 572426054-Dimethylthiocarbamoyloxy-3-fluoro-5-nitro-2-o-tolylamino-benzoic acid methyl ester

Procedure

The compound 4-dimethylthiocarbamoyloxy-2,3-difluoro-5-nitro-benzoic acid methyl ester is dissolved in excess o-toluidine. The stirring mixture is brought to 200° C. for one hour. The mixture is then poured into 5% aqueous hydrochloric acid. The aqueous mixture is extracted with diethyl ether. The organic phase is washed with water and brine, is dried over magnesium sulfate, and is concentrated in vacuo. The crude product is purified by ordinary methods such as chromatography or crystallization from an appropriate solvent.

Workup

  1. extractionThe aqueous mixture is extracted with diethyl ether
  2. washThe organic phase is washed with water and brine
  3. dry with materialis dried over magnesium sulfate
  4. concentrationis concentrated in vacuo
  5. customThe crude product is purified by ordinary methods such as chromatography or crystallization from an appropriate solvent

Sources & evidence

ORD record
ord-f9f6dacd0e184b4c9e298801ea377a8b
Source dataset
uspto-grants-2006_04
Patent number
US07030119B1

Reaction notes

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