N,N-Dimethylaniline → HCID 178423881, compound

HRID 742096Notes

Reaction equation

HRID 742096 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].CN(C)C1C=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 949N,N-DimethylanilineHCID 9999CyanogenHCID 124871862-Amino-1-(4-methylphenyl)ethan-1-one hydrochloride

Product 1

HCID 178423881HCID 178423881, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

15 g (81 mmol) of 2-amino-4'-methylacetophenone hydrochloride was measured out in a 200-ml four-necked flask. To the material was then added 121 ml (121 mmol) of a 1 mol/l N,N-dimethylformamide solution of cyanogen. The mixture was then stirred. To the mixture was then added 29.4 g (243 mmol) of N,N-dimethylaniline. The mixture was then heated at a temperature of 100° C. with stirring for 3 hours. N,N-dimethylaniline was then distilled off from the reaction mixture under a pressure of 30 mmHg. The reaction mixture was then allowed to cool to room temperature. 200 ml of water was then poured into the reaction mixture. The reaction mixture was acidified with hydrochloric acid, and a precipitate was recovered by filtration. The filtration residue was dissolved in 200 ml of a 5% aqueous solution of sodium hydroxide, and the solution was filtered. The filtrate was then acidified with hydrochloric acid. 2-Cyano-4-(p-tolyl)imidazole as a desired compound was then recovered by filtration. The material was then dried to obtain 12.43 g of a desired compound with a purity of 83.4% (yield: 70.0%).

Workup

  1. stirringwith stirring for 3 hours
  2. distillationN,N-dimethylaniline was then distilled off from the reaction mixture under a pressure of 30 mmHg
  3. temperatureto cool to room temperature
  4. addition200 ml of water was then poured into the reaction mixture
  5. filtrationa precipitate was recovered by filtration
  6. dissolutionThe filtration residue was dissolved in 200 ml of a 5% aqueous solution of sodium hydroxide
  7. filtrationthe solution was filtered
  8. filtration2-Cyano-4-(p-tolyl)imidazole as a desired compound was then recovered by filtration
  9. customThe material was then dried

Sources & evidence

ORD record
ord-086e7efb4a5c4d05b5c09c14a36791fc
Source dataset
uspto-grants-1996_09
Patent number
US05552557

Reaction notes

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