Imidazole → HCID 54133220, compound

HRID 128905Notes

Reaction equation

HRID 128905 reaction equation
CN(C=O)C.[NH:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]([O:13][N:14]=[C:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH3:12]>CCOCC>[CH2:11]([O:13][N:14]=[C:15]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 53990321HCID 53990321, compound

Product 1

HCID 54133220HCID 54133220, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

DMF (3 ml) and imidazole (0.41 g) were added to α-chloro-2-(4-chlorobenzylthio)benzaldehyde O-ethyloxime (0.68 g), and the mixture was stirred at 170° C. for 21 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with brine (80 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography and recrystallized from ethyl acetate/n-hexane to give 2-(4-chlorobenzylthio)-α-(1-imidazolyl)benzaldehyde O-ethyloxime (0.11 g) as colorless crystals. mp. 96.5°-97.5° C.

Workup

  1. additionwas added
  2. washthe mixture was washed with brine (80 ml) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel chromatography
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-4d067d30dedb4b81b3b0bb61cbd7a789
Source dataset
uspto-grants-1995_11
Patent number
US05466661

Reaction notes

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