Aluminum(III) Chloride → HCID 14537428, compound

HRID 1607714Notes

Reaction equation

HRID 1607714 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[O:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[N:12]1([C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1>C(Cl)Cl>[N:12]1([C:17]2[CH:18]=[CH:19][C:20]([C:21]([C:6]3[O:5][C:4](=[O:7])[NH:3][C:2]=3[CH3:1])=[O:22])=[CH:24][CH:25]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 145374264-Methyl-1,3-oxazol-2(3H)-oneHCID 145374274-(1H-Imidazol-1-yl)benzoyl chloride

Product 1

HCID 14537428HCID 14537428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 50 ml methylene chloride were placed 1.30 g (0.0132 mol) 4-methyl-2(3H)-oxazolone and 5.22 g (0.039 mol) aluminum chloride. The mixture was stirred 30 minutes and 2.72 g (0.0132 mol) 4-(1H-imidazol-1-yl)benzoyl chloride were added. The mixture was heated on the steam bath allowing the methylene chloride to evaporate, after which the residue was heated an additional 30 minutes. The residue was quenched with water and the water solution neutralized with sodium bicarbonate. The solution was evaporated to dryness and the residue was leached with hot methanol. Evaporation of the methanol provided the crude product which was purified by chromatography; m.p. 320°.

Workup

  1. temperatureThe mixture was heated on the steam bath
  2. customto evaporate
  3. temperatureafter which the residue was heated an additional 30 minutes
  4. customThe residue was quenched with water
  5. customThe solution was evaporated to dryness
  6. customEvaporation of the methanol

Sources & evidence

ORD record
ord-6e8b5027d5ed4cce8e445bc84645097c
Source dataset
uspto-grants-1989_09
Patent number
US04866182

Reaction notes

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