Ammonia → HCID 178424632, compound

HRID 619680Notes

Reaction equation

HRID 619680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:20]=1[CH:21]=O.C([O-])(=O)C.[NH4+:33].[NH3:34]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:34][C:21]([C:20]3[C:19]([CH3:18])=[CH:26][C:25]([CH3:27])=[CH:24][C:23]=3[CH3:28])=[N:33][C:9]=2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 102542,4,6-TrimethylbenzaldehydeHCID 517165Ammonium AcetateHCID 21847014HCID 21847014, compound

Product 1

HCID 178424632HCID 178424632, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 12.3 g of 1-(4-chlorophenyl)-2-pyridin-4-yl-ethanedione and 7.4 g of 2,4,6-trimethylbenzaldehyde in 125 ml of acetic acid containing 40 g of ammonium acetate was stirred at 100° C. for 2 hours, then left to cool to room temperature. The mixture was poured into a mixture of 300 ml of ice-water and 200 ml of concentrated ammonia solution and the mixture was extracted three times with ethyl acetate. After drying over anhydrous magnesium sulphate the solvent was evaporated. The residue was purified by chromatography on silica gel with dichloromethane/methanol (9:1) and crystallized from ethyl acetate to yield 6.7 g of 4-[5-(4-chlorophenyl)-2-(2,4,6-trimethyphenyl)imidazol-4-yl]pyridine, m.p. 275° C.

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  5. customwas evaporated
  6. customThe residue was purified by chromatography on silica gel with dichloromethane/methanol (9:1)
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-580ac4d43c5f4a5da0ccbe37690834c4
Source dataset
uspto-grants-1999_09
Patent number
US05959113

Reaction notes

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