Water → HCID 13019448, compound

HRID 1649186Notes

Reaction equation

HRID 1649186 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH:5]([N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)[CH:6]([OH:12])[C:7]([CH3:11])([CH3:10])[CH2:8][F:9].[C:23]([O-])(=[O:25])[CH3:24].[Na+].O>C(OC(=O)C)(=O)C>[ClH:1].[C:23]([O:12][CH:6]([C:7]([CH3:11])([CH3:10])[CH2:8][F:9])[CH:5]([O:4][C:3]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=1[Cl:1])[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 13019446HCID 13019446, compound

Product 1

HCID 13019448HCID 13019448, compoundYield 2,948.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

17.3 g (0.05 mol) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-butan-2-ol were dissolved in 100 ml of acetic anhydride and, after adding 0.1 g of sodium acetate, the mixture was stirred at 100° C. for 10 hours. Thereafter, the reaction solution was allowed to cooled to room temperature, stirred into 500 ml of water and left to stand for 15 hours. The aqueous phase was extracted twice with 200 ml of methylene chloride each time. The combined organic phases were washed with 100 ml each of sodium bicarbonate solution and water, dried over sodium sulphate and concentrated in vacuo. The residue was taken up in 100 ml of ether, 20 ml of ethereal hydrochloric acid were added, the solvent was distilled off in vacuo and the residue was stirred with 50 ml of ether. 15.3 g (72% of theory) of 2-acetoxy-1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-butane hydrochloride of melting point of 198°-200° C. were obtained.

Workup

  1. temperatureto cooled to room temperature
  2. waitleft
  3. waitto stand for 15 hours
  4. extractionThe aqueous phase was extracted twice with 200 ml of methylene chloride each time
  5. washThe combined organic phases were washed with 100 ml each of sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. addition20 ml of ethereal hydrochloric acid were added
  9. distillationthe solvent was distilled off in vacuo
  10. stirringthe residue was stirred with 50 ml of ether

Sources & evidence

ORD record
ord-7aa606b98daa418bae354965156d2f77
Source dataset
uspto-grants-1983_11
Patent number
US04415586

Reaction notes

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