Sodium Hydroxide → HCID 22916410, compound

HRID 265375Notes

Reaction equation

HRID 265375 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:15]=[C:14]1[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:32][CH:31]=1)=[O:5])C.[OH-].[Na+]>>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:15]=[C:14]1[C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:34][CH:35]=1)([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22916408HCID 22916408, compound

Product 1

HCID 22916410HCID 22916410, compoundYield 58.6%

Procedure

1-(7-Ethoxycarbonylheptyl)-2-[4-octyloxyphenyl]-4,5-diphenylimidazole (3.2 g) was reacted with 2N sodium hydroxide in a method similar to Example 9. Column chromatography on silica gel eluted with a dichloro-methane:methanol gradient and recrystallisation from acetonitrile gave 1-(7-carboxyheptyl)-2-[4-octyloxy-phenyl]-4,5-diphenylimidazole (1.7 g, 58.6%) as a white solid, m.p. 114°-115°. Found: C, 78.61; H, 8.23; N, 4.96%; C37H46N2O3 requires: C, 78.41; H, 8.18; N, 4.94%.

Workup

  1. washColumn chromatography on silica gel eluted with a dichloro-methane
  2. custommethanol gradient and recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-c4450cb1f9ca48d4b2dd513747fea9b6
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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