Acetic Acid → HCID 13849841, compound

HRID 1638246Notes

Reaction equation

HRID 1638246 reaction equation
B([O-])=O.[Na+].[Cl:5][CH:6]([Cl:27])[C:7]([CH3:26])([CH3:25])[C:8](=[O:24])[CH:9]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[N:10]1[CH:14]=[N:13][CH:12]=[N:11]1.C(O)(=O)C>CO>[Cl:27][CH:6]([Cl:5])[C:7]([CH3:25])([CH3:26])[CH:8]([OH:24])[CH:9]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[N:10]1[CH:14]=[N:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 145326Sodium metaborateHCID 13849842HCID 13849842, compound

Product 1

HCID 13849841HCID 13849841, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1.5 g (0.04 mole) of sodium boranate are added in portions to a solution of 8 g (0.02 mole) of 4,4-dichloro-1-(2,4-dichlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one in 80 ml of methanol at 20°-30° C., while stirring. After two hours, the mixture is brought to pH 6 by addition of acetic acid. The solution is evaporated under reduced pressure, the residue is taken up in 200 ml of methylene chloride and the mixture is washed three times with 400 ml of water each time and dried over sodium sulphate. After evaporating the solution and removing the residual solvent by warming the residue at 50° C. under 0.01 bar for two hours, 6 g (75% of theory) of 4,4-dichloro-1-(2,4-dichlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol are obtained as a 3:1 mixture of the two diastereomers in the form of a highly viscous oil.

Workup

  1. customThe solution is evaporated under reduced pressure
  2. washthe mixture is washed three times with 400 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. customAfter evaporating the solution
  5. customremoving the residual solvent

Sources & evidence

ORD record
ord-d292b3eab7e94669bafe9906512d4a63
Source dataset
uspto-grants-1989_11
Patent number
US04878939

Reaction notes

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