Pyridine → HCID 178423881, compound

HRID 742095Notes

Reaction equation

HRID 742095 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=O.[N:13]#[C:14][C:15]#[N:16].N1C=CC=CC=1>CN(C)C=O>[C:14]([C:15]1[NH:2][CH:3]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[N:16]=1)#[N:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9999CyanogenHCID 124871862-Amino-1-(4-methylphenyl)ethan-1-one hydrochloride

Product 1

HCID 178423881HCID 178423881, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2.0 g (11 mmol) of 2-amino-4'-methylacetophenone hydrochloride was measured out in a 100-ml round bottom flask. To the material was then added 40 ml (40 mmol) of a 1 mol/l N,N-dimethylformamide solution of cyanogen at a temperature of 0° C. To the mixture was then added 1.7 g (22 mmol) of pyridine. The mixture was then heated at a temperature of 60° C. with stirring for 18 hours. The reaction mixture was then allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate and water. The resulting organic phase was washed with saturated brine. The organic phase was dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography to obtain 1.55 g (yield: 77 %) of 2-cyano-4- (p-tolyl)imidazole.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate and water
  3. washThe resulting organic phase was washed with saturated brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b83493dfcc34a77bb6b5f9e7a253814
Source dataset
uspto-grants-1996_09
Patent number
US05552557

Reaction notes

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