Acetic Acid → 5-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-methylthiophene-2-carboxylic acid

HRID 2381860Notes

Reaction equation

HRID 2381860 reaction equation
[CH2:1]([C:8]1[NH:12][N:11]=[C:10]([C:13]2[S:17][C:16]([C:18]([O:20]CCCC)=[O:19])=[C:15]([CH3:25])[CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C>C(O)C.O>[CH2:1]([C:8]1[NH:12][N:11]=[C:10]([C:13]2[S:17][C:16]([C:18]([OH:20])=[O:19])=[C:15]([CH3:25])[CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59179697HCID 59179697, compound

Product 1

HCID 591797135-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-methylthiophene-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of butyl 5-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-methylthiophene-2-carboxylate (0.23 g, 0.64 mmol) and 1 N aqueous sodium hydroxide (3.8 mL, 3.8 mmol) in ethanol (7.6 mL) was stirred at reflux for 1 h. The reaction mixture was cooled to 0° C. and acidified with glacial acetic acid to pH 5-6, and diluted with water (25 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colorless solid (0.18 g, 96%): 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 7.45 (s, 1H), 7.37-7.20 (m, 6H), 4.12 (s, 2H), 2.47 (s, 3H); MS (ES+) m/z 300.21 (M+1).

Workup

  1. temperatureat reflux for 1 h
  2. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6acb971ce3f54e12ac5237a2fcd69d37
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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