Sodium Hydroxide → HCID 22916442, compound

HRID 1376360Notes

Reaction equation

HRID 1376360 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][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:15]=[C:14]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:16]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[N:15]=[C:14]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22916439HCID 22916439, compound

Product 1

HCID 22916442HCID 22916442, compoundYield 21.2%

Procedure

1-(7-Ethoxycarbonylheptyl)-4,5-bis(4-methoxyphenyl)-2-phenylimidazole (10 g) was reacted with 2N sodium hydroxide in a method similar to Example 10. The aqueous reaction mixture was evaporated to dryness in vacuo and the residue was mixed with ethanol (150 ml) and insoluble material was filtered off. The flitrate was evaporated to dryness and the residue was purified by column chromatography on silica gel eluted with a dichloromethane:methanol gradient. Further purification on Amberlite resin IRA-400 eluted with a methanol:water to methanol:2N HC1 gradient and recrystallisation from ethanol gave 1-(7-carboxyheptyl)-4,5-bis(4-methoxy-phenyl)-2-phenylimidazole (2.01 g, 21%) as a white solid, m.p. 149°-150°. Found: C, 74.50; H, 6.75; N, 5.69%; C31H34N2O4 0.5% w/w C2H5OH requires: C, 74.56; H, 6.90; N, 5.59%.

Workup

  1. customThe aqueous reaction mixture was evaporated to dryness in vacuo
  2. additionthe residue was mixed with ethanol (150 ml) and insoluble material
  3. filtrationwas filtered off
  4. customThe flitrate was evaporated to dryness
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluted with a dichloromethane
  7. customFurther purification on Amberlite resin
  8. washeluted with a methanol
  9. customwater to methanol:2N HC1 gradient and recrystallisation from ethanol

Sources & evidence

ORD record
ord-908920ff50874b7799b93d95731b7486
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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