1-Methylimidazole → HCID 15333086, compound

HRID 1721564Notes

Reaction equation

HRID 1721564 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.C([Li])CCC.[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19]>>[F:12][C:13]([F:24])([F:25])[O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1)=[O:19]

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 15333086HCID 15333086, compound

Procedure

In a flask was placed 1.0 g (12.2 mmol) 1-methylimidazole. Then, 5.1 ml (12.8 mmol) n-butyllithium was added dropwise and the mixture was stirred for 30 minutes. Then, 2.7 g (12.2 mmol) 3-trifluoromethoxybenzoyl chloride was added dropwise. The contents were mixed for 2 hours at -78° C., then allowed to warm to room temperature for an additional 2 hours. The mixture was quenched with water. The product was extracted with ether, dried and purified by flash chromatography (5-10% ethyl acetate/hexanes, silica gel) and was identified as the desired product by spectroscopic analyses.

Workup

  1. customIn a flask was placed
  2. additionThe contents were mixed for 2 hours at -78° C.
  3. customThe mixture was quenched with water
  4. extractionThe product was extracted with ether
  5. customdried
  6. custompurified by flash chromatography (5-10% ethyl acetate/hexanes, silica gel)

Sources & evidence

ORD record
ord-2386eb6d7604482a9bf187cd9ca4fa44
Source dataset
uspto-grants-1996_04
Patent number
US05512537

Reaction notes

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