HCID 22130193, compound → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-methyl-3-pyridinyl)methyl)-

HRID 1857753Notes

Reaction equation

HRID 1857753 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]2[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=2)[C:12]([S: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>C(O)C.Cl>[Cl:25][C:23]1[CH:24]=[C:19]([S:18][C:12]2[N:11]([CH2:27][C:28]3[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=3)[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:17])[CH3:16])[CH:20]=[C:21]([Cl:26])[CH:22]=1

Participants

4

Reactant 1

HCID 22130193HCID 22130193, compound

Product 1

HCID 4740621H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-methyl-3-pyridinyl)methyl)-Yield 99.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a mixture of 15 ml of ethanol and 20 ml of 36% hydrochloric acid was dissolved 609 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole (118a), and the mixture was stirred at 90° C. for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. An aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crystals were washed with diethyl ether, filtered, and 500 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(2-methyl pyridin-3-ylmethyl)-1H-imidazole (119a) was obtained (yield 99%). mp 136° C.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionAn aqueous sodium hydrogen carbonate solution was added
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe crystals were washed with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7277803611ee460f862933d44ba60392
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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