Ethanol → 2-Phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid

HRID 488791ノート

反応式

HRID 488791 の反応式
CC1[C:3]([C:13]([OH:15])=[O:14])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[OH-:16].[Na+].[O-][Mn](=O)(=O)=O.[K+].[CH2:24]([OH:26])[CH3:25]>O>[C:7]1([N:5]2[N:6]=[C:25]([C:24]([OH:16])=[O:26])[C:3]([C:13]([OH:15])=[O:14])=[N:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 5199365-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid

生成物 1

HCID 222680202-Phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid収率 95%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
23 °C

実験手順

A solution of 5-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (10.2 g, 50 mmol) and NaOH (17.6 g, 440 mmol) in water (375 mL) at 23° C. was treated with KMnO4 (30.8 g, 195 mmol). The resulting solution was heated at reflux for 17 h, cooled to 23° C. and treated with ethanol (50 mL). The resulting mixture was filtered to remove MnO2. The filtrate was acidified with HCl (conc.) to pH 1. The resulting white solid was collected by filtration. The filtrate was concentrated to half volume and more solid was collected by filtration. The two combined batches of solid were dried in vacuo to afford 11.1 g (95%) of 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 17 h
  3. filtrationThe resulting mixture was filtered
  4. customto remove MnO2
  5. filtrationThe resulting white solid was collected by filtration
  6. concentrationThe filtrate was concentrated to half volume and more solid
  7. filtrationwas collected by filtration
  8. customThe two combined batches of solid were dried in vacuo

出典と根拠

ORDレコード
ord-7b3667eafbd842b18f609f673d048241
出典データセット
uspto-grants-2005_12
特許番号
US06974813B2

反応ノート

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