Methane → 1-[2-(2-Chloro-6-methyl-3-pyridinyl)-5-methyl-1H-imidazol-4-yl]ethanone

HRID 615325Notes

Reaction equation

HRID 615325 reaction equation
[CH3:1][C:2](=O)[C:3](=[N:7]O)[C:4](=[O:6])[CH3:5].[Cl:10][C:11]1[C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=[C:13]([CH3:19])[N:12]=1.O.C>C(#N)C>[Cl:10][C:11]1[C:16]([C:17]2[NH:18][C:2]([CH3:1])=[C:3]([C:4](=[O:6])[CH3:5])[N:7]=2)=[CH:15][CH:14]=[C:13]([CH3:19])[N:12]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 962WaterHCID 20427660(2-Chloro-6-methylpyridin-3-YL)methanamineHCID 178468373HCID 178468373, compound

Product 1

HCID 133879381-[2-(2-Chloro-6-methyl-3-pyridinyl)-5-methyl-1H-imidazol-4-yl]ethanoneYield 18.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 0.7 g of 2,3,4-pentanetrione 3-oxime and 0.9 g of 2-chloro-6-methyl-3-pyridylmethylamine in 50 ml of acetonitrile was stirred at the reflux temperature for 4 hours. The reaction mixture was evaporated in vacuo to give an oil. The oil was boiled in 50 ml. of water, treated with activated charcoal and filtered. The filtrate was cooled at 5° C. to yield a precipitate. The precipitate was collected, washed with cold water and dried to give 0.25 g of the product of the Example as a white solid, mp 156°-158° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give an oil
  3. filtrationfiltered
  4. customto yield a precipitate
  5. customThe precipitate was collected
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-19991feeec2a4c3ca05fce67fea48d46
Source dataset
uspto-grants-1985_02
Patent number
US04499097

Reaction notes

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