Trichloroacetyl chloride → 1-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-imidazol-2-yl]-2,2,2-trichloroethanone

HRID 252009Notes

Reaction equation

HRID 252009 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1.[Cl:14][C:15]([Cl:20])([Cl:19])[C:16](Cl)=[O:17].C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[N:3]=[C:4]([C:16](=[O:17])[C:15]([Cl:20])([Cl:19])[Cl:14])[N:5]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 668538872-(4-bromo-1H-imidazol-1-yl)-3-chloropyridine

Product 1

HCID 668551881-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-imidazol-2-yl]-2,2,2-trichloroethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g of 2-(4-bromo-1H-imidazol-1-yl)-3-chloropyridine in 5 ml of dichloromethane was added dropwise a solution of 0.45 ml of trichloroacetyl chloride in 5 ml of dichloromethane at room temperature. The resulting mixture was stirred at room temperature for 1 day. Thereto 0.57 ml of triethylamine was added, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 1.0 g of 1-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-imidazol-2-yl]-2,2,2-trichloroethanone of the formula:

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b376b57b4978415ab3d3ac0b1ecb6017
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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