Sodium Hydroxide → HCID 10003259, compound

HRID 1376332Notes

Reaction equation

HRID 1376332 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][CH:33]=[CH:32][CH:31]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[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:19]=[CH:20][CH:21]=[CH:22][CH:23]=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][CH:33]=[CH:32][CH:31]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22916369HCID 22916369, compound

Product 1

HCID 10003259HCID 10003259, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(7-ethoxycarbonylheptyl)-2,4,5-triphenyl-imidazole (13.6 g), 2N aqueous sodium hydroxide (300 ml) and ethanol (200 ml ) was heated at reflux for 2.5 h. The ethanol was removed in vacuo and the reaction mixture was acidified with 2N aqueous hydrochloric acid. The aqueous solution was extracted with ethyl acetate (4×200 ml ) and the organic extracts were combined, dried over anhydrous magnesinm sulphate and evaporated to dryness in vacuo. Recrystallisation from ethanol gave 1-(7-carboxyheptyl)-2,4,5-triphenylimidazole (9.77 g, 76.4%) as a white solid, m.p. 162°; Found C, 79.43; H, 6.93; N, 6.36%; C29H30N2O2 requires: C, 79.42; H, 6.90; N, 6.39%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. customThe ethanol was removed in vacuo
  4. extractionThe aqueous solution was extracted with ethyl acetate (4×200 ml )
  5. dry with materialdried over anhydrous magnesinm sulphate
  6. customevaporated to dryness in vacuo
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-761ab28935634159958dcc8068467feb
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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