Hydrochloric Acid → HCID 19973111, compound

HRID 2380319Notes

Reaction equation

HRID 2380319 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:22])([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:10]([F:15])([F:14])[C:11]([NH2:13])=O.ClC(Cl)(Cl)C(Cl)=O.C(OCC)(=O)C.Cl>N1C=CC=CC=1.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:22])([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:10]([F:14])([F:15])[C:11]#[N:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6420Trichloroacetyl chlorideHCID 8857Ethyl AcetateHCID 9948882HCID 9948882, compound

Product 1

HCID 19973111HCID 19973111, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine was dissolved 150 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide. To the solution was added 100 mg of trichloroacetyl chloride at 0°-5° C. The resulting mixture was subjected to reaction at the same temperature for 2 hours. Then, the reaction mixture was introduced into a mixed solvent consisting of 10 ml of ethyl acetate and 5 ml of water. The resulting solution was adjusted to pH 2.0 with 6N 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=50/1) to obtain 100 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanenitrile.

Workup

  1. customThe resulting mixture was subjected to reaction at the same temperature for 2 hours
  2. additionThen, the reaction mixture was introduced into a mixed solvent
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by a column chromatography (eluant: chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-a7f80a17404340ce96693484501ee3e8
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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