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

HRID 2381809Notes

Reaction equation

HRID 2381809 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([C:19]([O:21]CC)=[O:20])=[C:16]([CH3:18])[N:17]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].C(O)(=O)C>O1CCCC1.O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([C:19]([OH:21])=[O:20])=[C:16]([CH3:18])[N:17]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 59179723ethyl 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 591796642-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate (0.23 g, 0.70 mmol) in a mixture of tetrahydrofuran (4 mL) and water (1 mL) was added lithium hydroxide (0.15 g, 3.51 mmol). The reaction mixture was stirred at ambient temperature for 18 hours and acidified to pH=6 with acetic acid. The white solid precipitated was collected by filtration, washed with water and dried in air to afford the title compound as a white solid (0.20 g, 95%): MS (ES+) m/z 301.2 (M+1).

Workup

  1. customThe white solid precipitated
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried in air

Sources & evidence

ORD record
ord-effb21859df2483faaf41f1d96e6829a
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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