Imidazole → HCID 23339880, compound

HRID 28262Notes

Reaction equation

HRID 28262 reaction equation
CS(O[CH2:6][C:7]([C:16]#[N:17])([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:8])(=O)=O.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.CN(C)C=O>O>[ClH:15].[C:16]([C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)([CH3:8])[CH2:6][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)#[N:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 233398692-Cyano-2-(4-chlorophenyl)propyl methane sulfonate

Product 1

HCID 23339880HCID 23339880, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-cyano-2-(4-chlorophenyl)propyl methane sulfonate (63 g., 0.23 mole), imidazole (62.6 g., 0.9 mole) and N,N-dimethylformamide (3 ml.) is heated with stirring at 130° C. for 24 hours. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are washed with water and dried over magnesium sulfate. Into the ethereal solution is bubbled dry hydrogen chloride gas. The white solid which precipitate is collected and dried to give 38 g. (58.6%) of the expected product, which is identified by nmr.

Workup

  1. temperatureis heated
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. customInto the ethereal solution is bubbled dry hydrogen chloride gas
  6. customThe white solid which precipitate is collected
  7. customdried
  8. customto give 38 g

Sources & evidence

ORD record
ord-5cd0d87225b84146bca1b93315c263fc
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Reaction notes

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