Acetyl chloride → HCID 13504103, compound

HRID 1789340Notes

Reaction equation

HRID 1789340 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)([OH:17])[CH:10]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH3:11])=[CH:5][CH:4]=1.[H-].[Na+].[C:32](Cl)(=[O:34])[CH3:33]>CN(C)C=O.O>[C:32]([O:17][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=1)([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=1)[CH:10]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[CH3:11])(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 13504093HCID 13504093, compound

Product 1

HCID 13504103HCID 13504103, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,1-Bis-(4-trifluoromethylphenyl)-2-(1,2,4-1H- triazol-1-yl)propan-1-ol (0.5 g.) was added carefully to a suspension of sodium hydride (60 mg., freed from dispersion in oil by washing with hexane) in dry dimethylformamide (20 cm3) under a nitrogen atmosphere. After stirring the mixture for 2 hours acetyl chloride (0.1 g) was added and after a further 2 hours the mixture was diluted with water and extracted with chloroform. The chloroform layer was separated, washed with water, dried over anhydrous magnesium sulphate, and concentrated by evaporation of the solvent under reduced pressure to yield a residual oil which was purified by hplc and which solidified on trituration with petroleum ether (boiling range 60°-80° C.) to yield 1,1-bis(4-trifluoromethylphenyl)-2-(1,2,4-1H-triazol1-yl)propyl acetate (160 mg.).

Workup

  1. additionwas added and after a further 2 hours the mixture
  2. extractionextracted with chloroform
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated by evaporation of the solvent under reduced pressure
  7. customto yield a residual oil which
  8. customwas purified by hplc and which

Sources & evidence

ORD record
ord-5b343c9424bd4933834810374e403f9e
Source dataset
uspto-grants-1987_08
Patent number
US04689337

Reaction notes

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