Imidazole → 2-(2,4-Dichlorophenyl)-1-(1H-imidazol-1-yl)-2-methoxypentan-1-one

HRID 2412566Notes

Reaction equation

HRID 2412566 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[CH3:7][O:8][C:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])([CH2:13][CH2:14][CH3:15])[C:10](Cl)=[O:11]>C(#N)C>[CH3:7][O:8][C:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])([CH2:13][CH2:14][CH3:15])[C:10]([N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1)=[O:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5360545SodiumHCID 13385917HCID 13385917, compound

Product 1

HCID 133372632-(2,4-Dichlorophenyl)-1-(1H-imidazol-1-yl)-2-methoxypentan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 20 ml of acetonitrile was added 2.3 g of the sodium salt of imidazole, and 7.0 g of α-methoxy-α-n-propyl-2,4-dichlorophenylacetic acid chloride was then added dropwise at room temperature. The mixture was stirred for 2 hours, poured into 200 ml of ice water and extracted with 300 ml of chloroform. The extract was concentrated under reduced pressure, and the oily product obtained was purified by column chromatography on silica gel to obtain 2.5 g of N-(α-methoxy-α-n-propyl-2,4-dichlorophenylacetyl)imidazole (compound No. 43). m.p. 99°-101° C.

Workup

  1. additionwas then added dropwise at room temperature
  2. extractionextracted with 300 ml of chloroform
  3. concentrationThe extract was concentrated under reduced pressure
  4. customthe oily product obtained
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-66bf8127974b4ac882062038ef0b62b1
Source dataset
uspto-grants-1985_01
Patent number
US04493842

Reaction notes

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