Benzoyl chloride → HCID 22258292, compound

HRID 1610835Notes

Reaction equation

HRID 1610835 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH3:9])[NH:6][C:7]=1[CH3:8])[CH3:2].[C:10]([Cl:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[ClH:18].[CH2:1]([C:3]1[N:4]=[C:5]([CH2:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:17])[NH:6][C:7]=1[CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 157240865-Ethyl-2,4-dimethyl-1H-imidazole

Product 1

HCID 22258292HCID 22258292, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound is prepared as described in example X (step 4 and 5) with 1.00 g (8.05 mmol) 4-Ethyl-2,5-dimethyl-1H-imidazole (example XIII, step 1), 3.74 g (26.57 mmol) of benzoyl chloride and 2.85 g (28.18 mmol) of TEA in 20 ml acetonitrile. After reaction the solvent is evaporated under vacuum. The residue is extracted with toluene/water and the water phase is filtrated over a silica-layer. The solvent is evaporated under vacuum. The crude intermediate is directly transformed into 2-(4-Ethyl-5-methyl-1H-imidazol-2-yl)-1-phenylethanone hydrochloride. After the reaction the solvent is evaporated under vacuum. The residue is extracted with ethyl acetate/water. The water phase is concentrated.

Workup

  1. customThe compound is prepared
  2. customAfter reaction the solvent
  3. customis evaporated under vacuum
  4. extractionThe residue is extracted with toluene/water
  5. filtrationthe water phase is filtrated over a silica-layer
  6. customThe solvent is evaporated under vacuum
  7. customAfter the reaction the solvent
  8. customis evaporated under vacuum
  9. extractionThe residue is extracted with ethyl acetate/water
  10. concentrationThe water phase is concentrated

Sources & evidence

ORD record
ord-8e24d90ed3234f5f9f0c5c6110af8157
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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