Methanol → HCID 20497976, compound

HRID 2166831Notes

Reaction equation

HRID 2166831 reaction equation
C[OH:2].[Cl:3][C:4]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:5]=1[C:6](=O)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[BH4-].[Na+]>>[OH:2][CH:7]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[CH2:6][C:5]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:4]=1[Cl:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 322321-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 20497976HCID 20497976, compound

Procedure

A 150 ml solution of methanol containing 15.6 g (0.061 mole) of 1-(2,4-dichlorophenacyl) imidazole cooled to 0°-5° C. was treated with 1.38 g (0.037 mole) of sodium borohydride in portions. The reaction was stirred 1/2 hour and the methanol removed at reflux while adding 100 ml of H2O. The refluxing aqueous mixture was treated with 16 ml of conc. HCl, cooled, and treated with 50 ml of conc. NH4OH. The mixture was extracted with methylene chloride, dried over MgSO4, and concentrated to give 11.3 g of a white solid product (66.8%), m.p. 139°-141° C. (from ethanol).

Workup

  1. customthe methanol removed
  2. temperatureat reflux
  3. additionwhile adding 100 ml of H2O
  4. additionThe refluxing aqueous mixture was treated with 16 ml of conc. HCl
  5. temperaturecooled
  6. additiontreated with 50 ml of conc. NH4OH
  7. extractionThe mixture was extracted with methylene chloride
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d3051995b0b24fd4ac2a4b3e814b5c21
Source dataset
uspto-grants-1983_06
Patent number
US04389409

Reaction notes

Loading…