Hydrochloric Acid → HCID 22130877, compound

HRID 1857734Notes

Reaction equation

HRID 1857734 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH3:27])[C:12]([CH2:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.Cl>C(O)C>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([Cl:25])[CH:22]=1)[CH2:18][C:12]1[N:11]([CH3:27])[C:10]([CH2:9][OH:8])=[N:14][C:13]=1[CH:15]([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22130078HCID 22130078, compound

Product 1

HCID 22130877HCID 22130877, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

In 3 ml of ethanol was dissolved 470 mg (1.17 mmol) of 2-benzyloxymethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (58), followed by addition of 10 ml of concentrated hydrochloric acid (36% aqueous solution), and the mixture was refluxed under heating at 110° C. After 3 hours, the reaction mixture was concentrated under reduced pressure, neutralized with aqueous sodium hydroxide, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. To the crude crystals, 5 ml of diethyl ether was added, and filtered to give 350 mg of [5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (59a) (yield 95.9%).

Workup

  1. temperaturethe mixture was refluxed
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. additionTo the crude crystals, 5 ml of diethyl ether was added
  9. filtrationfiltered

Sources & evidence

ORD record
ord-268a47f2c1614fcb81f3cf5e314d73fe
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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