Sodium Hydroxide → 1-(7-Carboxyheptyl)-4,5-bis-(2-chlorophenyl)imidazole

HRID 265382Notes

Reaction equation

HRID 265382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19].[OH-].[Na+]>>[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:11]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=[CH:10]1)([OH:29])=[O:28]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 229164054,5-Bis(2-chlorophenyl)-1-(7-ethoxycarbonyl-heptyl)imidazole

Product 1

HCID 229164061-(7-Carboxyheptyl)-4,5-bis-(2-chlorophenyl)imidazoleYield 67%

Procedure

4,5-Bis(2-chlorophenyl)-1-(7-ethoxycarbonylheptyl)-imidazole (0.4 g) was reacted with 2N sodium hydroxide in a method similar to Example 10. Work-up and chromatography on silica gel eluted with a dichloromethane:methanol gradient followed by recrystallisation from dichloro-methane and hexane gave 1-(7-carboxyheptyl)-4,5-bis-(2-chlorophenyl)imidazole (0.25 g, 67%) as a white solid, m.p. 145°-6°.

Workup

  1. washchromatography on silica gel eluted with a dichloromethane
  2. custommethanol gradient followed by recrystallisation from dichloro-methane and hexane

Sources & evidence

ORD record
ord-cb045659157d419ba3bcccd0db8878b0
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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