Sodium Bicarbonate → 1-[3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanone

HRID 1019253Notes

Reaction equation

HRID 1019253 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:11]([CH:12]([OH:14])[CH3:13])=[C:10]([Cl:15])[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:14])[CH3:13])=[C:10]([Cl:15])[N:9]=[C:8]2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 184001141-[3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanol

Product 1

HCID 184001221-[3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanoneYield 54.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

3.7 g of 1-[3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanol is dissolved in 20 ml of acetic acid and slowly treated at 15° C. with a solution of 15.6 g of (NH4)2Ce(NO3)-6 in 30 ml of water. The mixture is stirred at 10° C. for 30 minutes, then allowed to warm to RT. It is diluted with 200 ml of water and adjusted to pH=5 using NaHCO3, and the product is filtered off with suction. Chromatography once each with DIP and MTB yields 2.0 g of a colorless oil.

Workup

  1. temperatureto warm to RT
  2. filtrationthe product is filtered off with suction

Sources & evidence

ORD record
ord-f58fed91320d46af89a2a8d8b4d9372a
Source dataset
uspto-grants-2002_11
Patent number
US06486189B2

Reaction notes

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