Pyridine → HCID 178423881, compound

HRID 742094Notes

Reaction equation

HRID 742094 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.N1C=CC=CC=1.[N:19]#[C:20][C:21]#[N:22]>C1(C)C=CC=CC=1>[C:20]([C:21]1[NH:2][CH:3]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[N:22]=1)#[N:19]

Participants

5

Reactant 3

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

Product 1

HCID 178423881HCID 178423881, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

0.93 g (5 mmol) of 2-amino-4'-methylacetophenone hydrochloride was suspended in 30 ml of toluene in a 50-ml stainless steel autoclave. To the suspension was then added 0.79 g (10 mmol) of pyridine. The suspension was then cooled to a temperature of -78° C. To the suspension was then added about 0.5 g (9.6 mmol) of cyanogen which had been cooled and solidified at a temperature of -78° C. The autoclave was then sealed. The suspension was heated at a temperature of 100° C. for 2.5 hours, and then allowed to cool. The content was then taken out of the autoclave. The reaction mixture was then extracted with ethyl acetate and water. The resulting organic phase was dried over anhydrous sodium sulfate, and then subjected to silica gel column chromatography to obtain 0.48 g (yield: 52 %) of 2-cyano-4-(p-tolyl)imidazole.

Workup

  1. temperaturehad been cooled
  2. customsolidified at a temperature of -78° C
  3. customThe autoclave was then sealed
  4. temperatureThe suspension was heated at a temperature of 100° C. for 2.5 hours
  5. temperatureto cool
  6. extractionThe reaction mixture was then extracted with ethyl acetate and water
  7. dry with materialThe resulting organic phase was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-1de6b473d41840ec8cf9db4336803225
Source dataset
uspto-grants-1996_09
Patent number
US05552557

Reaction notes

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