Acetyl chloride → HCID 69039095, compound

HRID 433585Notes

Reaction equation

HRID 433585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH2:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH:15][C:23](=[O:25])[CH3:24])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23445012HCID 23445012, compound

Product 1

HCID 69039095HCID 69039095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,4-dichlorophenyl)-1H-imidazole-4-methanamine (0.20 g, 0.83 mmol) in THF (30 ml) was added triethylamine (0.079 g, 0.78 mmol) and acetyl chloride (0.082 mg, 1.0 mmol). The reaction mixture was stirred at rt for 12 h. After evaporation of the solvent, the residue was dissolved in AcOEt and washed with H2O. The organic phase was dried (Na2SO4), concentrated and the obtained crude product was chromatographed [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]. The title compound was obtained as an off-white crystalline material (0.17 g, 74%). Mp. 177-180° C. (MeOH/CH2Cl2), MS: m/e=284 (M+H+).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe obtained crude product
  7. customwas chromatographed
  8. wash[silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]

Sources & evidence

ORD record
ord-21ca9cbd1739468d9d639edb761afc27
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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