Water → HCID 17838758, compound

HRID 1293124Notes

Reaction equation

HRID 1293124 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[CH:12][NH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([S:8][C:9]1[N:13]=[CH:12][N:11]([C:16](=[O:17])[N:15]([CH3:19])[CH3:14])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 178420436HCID 178420436, compound

Product 1

HCID 17838758HCID 17838758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-benzylthio-1H-1,2,4-triazole (172 mg), dimethylcarbamoyl chloride (248 μl) and anhydrous potassium carbonate (621 mg) in dimethylformamide (4 ml) was stirred at room temperature for 80 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed three times with water and subsequently once with saturated aqueous sodium chloride solution, and then dried over sodium sulfate. After filtration, the solvent was distilled from the filtrate under reduced pressure to obtain a clear oil. The resultant oil was purified by a column chromatography (ethyl acetate/hexane=1/5) to yield the titled compound (88 mg) as a clear oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed three times with water
  3. dry with materialsubsequently once with saturated aqueous sodium chloride solution, and then dried over sodium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled from the filtrate under reduced pressure
  6. customto obtain a clear oil
  7. customThe resultant oil was purified by a column chromatography (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-5aa516a544374f68b890b270683d55ec
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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