Imidazole → HCID 13247703, compound

HRID 543319Notes

Reaction equation

HRID 543319 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:11][N:10]=1>CN(C)C=O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:12]2[CH:13]=[CH:14][C:9]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)=[N:10][CH:11]=2)=[O:23])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 20145731(4-Chlorophenyl)(6-chloro-3-pyridinyl)methanone

Product 1

HCID 13247703HCID 13247703, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 13 g of sodium hydride (60% dispersion in mineral oil) in 240 ml of dimethylformamide is added 20 g of imidazole over a 15 minute period under occasional ice cooling. After the mixture is stirred at room temperature for an hour, 60 g of 2-chloro-5-(4-chlorobenzoyl)pyridine is added. The whole mixture is heated to 35° C. and an exothermic reaction starts. When the temperature rises at 60° C., the mixture is ice-cooled and then stirred at room temperature for an hour. The reaction mixture is poured into ice-cold water, the crystals precipitated are filtered off and recrystallized from ethanol to give 58 g of 5-(4-chlorobenzoyl)-2-(1-imidazolyl)pyridine as white crystals, melting at 155°-156° C.

Workup

  1. temperatureThe whole mixture is heated to 35° C.
  2. customan exothermic reaction
  3. customrises at 60° C.
  4. temperaturecooled
  5. stirringstirred at room temperature for an hour
  6. additionThe reaction mixture is poured into ice-cold water
  7. customthe crystals precipitated
  8. filtrationare filtered off
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-271a4ac0141944328cc2928ff2c59d50
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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