Acetyl chloride → HCID 69039450, compound

HRID 397868Notes

Reaction equation

HRID 397868 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH2:20])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][C:28](=[O:30])[CH3:29])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 69040616HCID 69040616, compound

Product 1

HCID 69039450HCID 69039450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl-methyl]-1H-imidazol-2-ylamine (1.0 g, 3.2 mmol) in THF (32 ml) was treated at rt with triethylamine (0.33 g, 3.2 mmol) and acetyl chloride (0.25 g, 3.2 mmol). The mixture was stirred at rt for 2 h, filtered and the organic phase was evaporated to dryness. After chromatography [silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] the title compound (0.19 g, 17%) was isolated as a light brown solid. Mp.>236° C. dec.(AcOEt), MS: m/e=350 (M+H+).

Workup

  1. filtrationfiltered
  2. customthe organic phase was evaporated to dryness
  3. washAfter chromatography [silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] the title compound (0.19 g, 17%)
  4. customwas isolated as a light brown solid

Sources & evidence

ORD record
ord-4af1a2030baa44ecb520c98eb9cd26e2
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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