Hydrochloric Acid → HCID 19973118, compound

HRID 1451938Notes

Reaction equation

HRID 1451938 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:17][CH2:16]1)[C:10]([F:15])([F:14])[C:11]([NH2:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1.Cl>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:17])([CH2:16][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C:10]([F:15])([F:14])[C:11]([NH2:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19973116HCID 19973116, compound

Product 1

HCID 19973118HCID 19973118, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 8 ml of N,N-dimethylformamide was dissolved 0.8 g of 3-(2,4-dichlorophenyl)-3,4-epoxy-2,2-difluorobutanamide. To the resulting solution were added 0.59 g of anhydrous potassium carbonate and 0.29 g of 1,2,4-triazole. The mixture was subjected to reaction at 80°-90° C. for 1 hour. The solvent was removed by distillation under reduced pressure. To the residue obtained were added 10 ml of ethyl acetate and 10 ml of water. The mixture was adjusted to pH 1.0 with 2N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: chloroform/methanol=100/1) to obtain 0.40 g of 3-(2,4-dichlorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide.

Workup

  1. customThe mixture was subjected to reaction at 80°-90° C. for 1 hour
  2. customThe solvent was removed by distillation under reduced pressure
  3. customTo the residue obtained
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThereafter, the solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluant: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-a0ac35dad84544f2ba8eea6098cee2f0
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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