Water → 1-(8-Carboxyoctyl)-2,4,5-triphenylimidazole

HRID 265363Notes

Reaction equation

HRID 265363 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)#N.S(=O)(=O)(O)[OH:35].[OH2:39]>>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([OH:35])=[O:39]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 229164431-(8-Cyanooctyl)-2,4,5-triphenyl-imidazole

Product 1

HCID 99813231-(8-Carboxyoctyl)-2,4,5-triphenylimidazoleYield 26%

Procedure

A mixture of 1-(8-cyanooctyl)-2,4,5-triphenyl-imidazole (0.8 g), concentrated sulphuric acid (10 ml) and water (10 ml) was stirred at reflux for 4 h. Water (50 ml) was added to the cooled mixture and the mixture was extracted with ethyl acetate (2×25 ml). The organic extracts were combined, washed with water (25 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Recrystallisation from ethanol/water gave 1-(8-carboxyoctyl)-2,4,5-triphenylimidazole (0.22 g, 26%) as a cream solid, m.p. 149°-150° C.; Found C: 79.32; H, 7.17; N, 5.95%; C30H32N2 requires: C, 79.61; H, 7.13; N, 6.19%.

Workup

  1. temperatureat reflux for 4 h
  2. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  3. washwashed with water (25 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness in vacuo
  6. customRecrystallisation from ethanol/water

Sources & evidence

ORD record
ord-bd4c72b423214d1f8cfd7693292d95f0
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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