Acetic Anhydride → HCID 13051756, compound

HRID 851683Notes

Reaction equation

HRID 851683 reaction equation
[Cl:1][C:2]([Cl:18])([Cl:17])[CH:3]([OH:16])[CH:4]([N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)[C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[Cl:18][C:2]([Cl:1])([Cl:17])[CH:3]([O:16][C:19](=[O:21])[CH3:20])[CH:4]([N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)[C:5](=[O:10])[C:6]([CH3:8])([CH3:9])[CH3:7]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 12902576HCID 12902576, compound

Product 1

HCID 13051756HCID 13051756, compoundYield 43%

Procedure

314.6 g (1 mol) of 1,1,1-trichloro-2-hydroxy-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one were heated at 95° C. in 1,000 ml of acetic anhydride for 30 hours. The excess anhydride was then distilled off in vacuo, the residue was taken up in 750 ml of methylene chloride and the methylene chloride mixture was washed with 10% strength sodium bicarbonate solution until neutral. The organic phase was dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue was stirred with 150 ml of diisopropyl ether. 153.8 g (43% of theory) of 1,1,1-trichloro-2-acetoxy-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one were obtained as the pure diastereomer of the A* form of melting point 129°-131° C.

Workup

  1. distillationThe excess anhydride was then distilled off in vacuo
  2. washthe methylene chloride mixture was washed with 10% strength sodium bicarbonate solution until neutral
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent in vacuo

Sources & evidence

ORD record
ord-3564c141f7e04734a6c4441b275f9a76
Source dataset
uspto-grants-1983_05
Patent number
US04386088

Reaction notes

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