Dimethylformamide → HCID 54001055, compound

HRID 1489390Notes

Reaction equation

HRID 1489390 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C=O)C.[Cl:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][O:26][C:27]2[CH:40]=[CH:39][CH:38]=[CH:37][C:28]=2[C:29]([N:32]2[CH:36]=[CH:35][N:34]=[CH:33]2)=[N:30][OH:31])=[CH:23][CH:22]=1>CCOCC>[CH2:7]([O:31][N:30]=[C:29]([N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)[C:28]1[CH:37]=[CH:38][CH:39]=[CH:40][C:27]=1[O:26][CH2:25][C:24]1[CH:41]=[CH:42][C:21]([Cl:20])=[CH:22][CH:23]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 74003411HCID 74003411, compound

Product 1

HCID 54001055HCID 54001055, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.21 g), benzyl chloride (0.15 g) and DMF (2 ml) were added to 2-(4-chlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde oxime (0.33 g), and the mixture was stirred at 60° C. for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was extracted 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 to give 2-(4-chlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde O-benzyloxime (0.38 g) as colorless crystals. mp. 94°-95.5° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted 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

Sources & evidence

ORD record
ord-acfa8e6df3ab4c248431f728d3925e7f
Source dataset
uspto-grants-1997_10
Patent number
US05677465

Reaction notes

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