Imidazole → HCID 54272954, compound

HRID 128908Notes

Reaction equation

HRID 128908 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.C(Cl)Cl.[Cl:13][C:14]1[CH:32]=[CH:31][C:17]([CH2:18][O:19][C:20]2[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=2[C:22]([NH:24][O:25][CH3:26])=O)=[CH:16][CH:15]=1>O>[CH3:26][O:25][N:24]=[C:22]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[C:21]1[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=1[O:19][CH2:18][C:17]1[CH:31]=[CH:32][C:14]([Cl:13])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 22904491HCID 22904491, compound

Product 1

HCID 54272954HCID 54272954, compoundYield 1.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (0.16 ml) was added to a suspension of imidazole (0.63 g) and methylene chloride (6 ml) under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes. Then 2-(4-chlorobenzyloxy)-N-methoxybenzamide (0.44 g) was added, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with methylene chloride (50 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to give 2-(4-chlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde O-methyloxime (0.01 g) as colorless crystals. mp. 92.5°-93.5° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringthe mixture was stirred
  4. temperatureunder reflux for 2 hours
  5. additionwas added
  6. extractionthe mixture was extracted with methylene chloride (50 ml) twice
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0f351cf2dcf04062ad8d4f59527c8deb
Source dataset
uspto-grants-1995_11
Patent number
US05466661

Reaction notes

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