Benzoyl chloride → HCID 57801500, compound

HRID 2101505Notes

Reaction equation

HRID 2101505 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH2:11].CCN(CC)CC.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:15][C:13]1[CH:12]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:14]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57801504HCID 57801504, compound

Product 1

HCID 57801500HCID 57801500, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylamine was dissolved in CH2Cl2 and Et3N was added followed by benzoyl chloride. The reaction mixture was stirred at room temperature for 2 h and washed with 1N HCl, saturated NaHCO3 and water. The organic phase was dried over Na2SO4 and concentrated. The residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH to afford N-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-benzamide (40 mg, 56%).

Workup

  1. washwashed with 1N HCl, saturated NaHCO3 and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-825c9c1633fe4f048ed8d147b6131260
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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