HCID 67558459, compound → 2(1H)-Pyridinone, 5-((5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-

HRID 1416060Notes

Reaction equation

HRID 1416060 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]2[CH:29]=[N:30][C:31](=[O:34])[CH2:32][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[CH:29]=[N:30][C:31](=[O:34])[CH2:32][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 67558459HCID 67558459, compound

Product 1

HCID 4740592(1H)-Pyridinone, 5-((5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-Yield 24.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a mixture of 5 ml of ethanol and 10 ml of 36% hydrochloric acid was dissolved 50 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(5,6-dihydro-6-oxopyridin-3-ylmethyl)-4-isopropyl-1H-imidazole, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. An aqueous sodium hydrogen carbonate solution was added, the mixture was 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 10 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(5,6-dihydro-6-oxopyridin-3-ylmethyl)-4-isopropyl-1H-imidazole (116a)was obtained (yield 24%). mp 220° 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. extractionthe mixture was extracted 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-dbfa287761fb4ca0b1e87a17cdeeec2c
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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