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

HRID 992395Notes

Reaction equation

HRID 992395 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-0b5a0eeb30b14648b44d486d3804ef00
Source dataset
uspto-grants-2002_10
Patent number
US06469004B1

Reaction notes

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