Water → 2-(8-Carboxyoctyl)-4,5-diphenyltriazole

HRID 265408Notes

Reaction equation

HRID 265408 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12]1)#N.S(=O)(=O)(O)[OH:29].[OH2:33]>>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12]1)([OH:29])=[O:33]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 229164262-(8-Cyanooctyl)-4,5-diphenyltriazole

Product 1

HCID 229163592-(8-Carboxyoctyl)-4,5-diphenyltriazoleYield 75%

Procedure

2-(8-Cyanooctyl)-4,5-diphenyltriazole (3.0 g) was treated with sulphuric acid (50 ml) and water (50 ml) and the mixture heated at reflux temperature for 4 hours. Water (200 ml) was added and the cooled mixture was extracted with ethyl acetate (3×75 ml), and the organic extracts combined and evaporated to give a solid. Recrystallisation from ethanol and water gave 2-(8-carboxyoctyl)-4,5-diphenyltriazole (2.37 g, 75%) as a white solid m.p. 84°-85° C. Found: C, 72.92; H, 7.20; N, 11.07%; C23H27N3O2 requires: C, 73.18; H, 7.21; N, 11.13%.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 4 hours
  3. extractionthe cooled mixture was extracted with ethyl acetate (3×75 ml)
  4. customevaporated
  5. customto give a solid
  6. customRecrystallisation from ethanol and water

Sources & evidence

ORD record
ord-2b91143e80a04566a951c8459915976b
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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