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

HRID 1416063Notes

Reaction equation

HRID 1416063 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-methylpyridin-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-515b7ae91c8f4bdc8292330357d2e3a1
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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