Imidazole → 1-[2-Cyano-2-(2,4-dichlorophenyl)hexyl]imidazole hydrochloride

HRID 28256Notes

Reaction equation

HRID 28256 reaction equation
CS(O[CH2:6][C:7]([C:20]#[N:21])([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:8][CH2:9][CH2:10][CH3:11])(=O)=O.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.CN(C)C=O>O>[ClH:18].[C:20]([C:7]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:6][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)#[N:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 233399252-Cyano-2-(2,4-dichlorophenyl)hexyl methane sulfonate

Product 1

HCID 233399171-[2-Cyano-2-(2,4-dichlorophenyl)hexyl]imidazole hydrochlorideYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-cyano-2-(2,4-dichlorophenyl)hexyl methane sulfonate (100 g., 0.29 mole), imidazole (100 g., 1.5 mole) and N,N-dimethylformamide (5 ml.) is heated with stirring at 135° C. overnight. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are dried over magnesium sulfate. The drying agent is filtered and into the ethereal solution is bubbled dry hydrogen chloride gas. The white solid which precipitates is collected and dried to give 70.4 g. (68%) of the expected product, which is identified by nmr.

Workup

  1. temperatureis heated
  2. extractionextracted with ether
  3. dry with materialThe combined ether extracts are dried over magnesium sulfate
  4. filtrationThe drying agent is filtered and into the ethereal solution
  5. customis bubbled dry hydrogen chloride gas
  6. customThe white solid which precipitates
  7. customis collected
  8. customdried
  9. customto give 70.4 g

Sources & evidence

ORD record
ord-ba867d69358d4678ae07e3c7210e9ee7
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Reaction notes

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