Imidazole → HCID 23339936, compound

HRID 28268Notes

Reaction equation

HRID 28268 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]Br)#[N:2].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.CN(C)C=O>O>[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)#[N:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 23339873HCID 23339873, compound

Product 1

HCID 23339936HCID 23339936, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-cyano-6-(2,4-dichlorophenyl)decyl bromide (14.2g., 0.036 mole) imidazole (10g., 0.15 mole) and 5 ml. N,N-dimethylformamide is heated at 120° C. for 24 hours. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are dried over magnesium sulfate and filtered. Into the ethereal solution is bubbled dry hydrogen chloride gas until no more oily precipitate forms. The solvent is then decanted and the oily residue is taken up in acetone and neutralized with dilute ammonium hydroxide solution. The purified free base is extracted into ether and dried over magnesium sulfate. When the solvent is evaporated, a total of 6.5 g. (47.8%) of product is obtained, which is identified by nmr.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined ether extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. customInto the ethereal solution is bubbled dry hydrogen chloride gas until no more oily precipitate forms
  5. customThe solvent is then decanted
  6. extractionThe purified free base is extracted into ether
  7. dry with materialdried over magnesium sulfate
  8. customWhen the solvent is evaporated

Sources & evidence

ORD record
ord-01d526c28d0343faaf6133d71910b692
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Reaction notes

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