Hydrochloric Acid → HCID 54284090, compound

HRID 1702463Notes

Reaction equation

HRID 1702463 reaction equation
[Cl-].[Ca+2].[Cl-].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12](=[O:27])[C:13]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[CH:14][C:15]1([CH3:21])[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16]1.[BH4-].[Na+].Cl>CO.CC(C)=O.O>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH:12]([OH:27])[C:13]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[CH:14][C:15]1([CH3:21])[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 53882710HCID 53882710, compound

Product 1

HCID 54284090HCID 54284090, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
-20 °C

Procedure

3.05 g (0.025 mole) of calcium chloride were added to 18.1 g (0.05 mole) of 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)-3-(methylcyclohex-3-en-1-yl)-2-propen-1-one in 100 ml of methanol, and the mixture was cooled to -20° C. 1.9 g (0.05 mole) of sodium borohydride were added in portions, and, when the addition had ended, the mixture was warmed to -10° C. Thereafter, an acetone/water mixture was added dropwise and the reaction mixture was allowed to warm to room temperature. It was adjusted to a pH value of 5 with dilute hydrochloric acid and concentrated. The residue was taken up in a mixture of methylene chloride/water and the organic phase was separated off, dried over sodium sulphate, filtered and concentrated. 15.6 g (85.7% of theory) of 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)-3-(methyl-cyclohex-3-en-1-yl)-2-propen-1-ol were obtained as an amorphous powder.

Workup

  1. additionthe addition
  2. temperaturethe mixture was warmed to -10° C
  3. temperatureto warm to room temperature
  4. concentrationconcentrated
  5. additionThe residue was taken up in a mixture of methylene chloride/water
  6. customthe organic phase was separated off
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7717982a5ae74b01952c8803f8061ecf
Source dataset
uspto-grants-1983_04
Patent number
US04381310

Reaction notes

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