Sodium Hydroxide → 2-(1H-1,2,3,4-tetrazol-5-yl)benzoic acid

HRID 976579ノート

反応式

HRID 976579 の反応式
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C(O)C>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([OH:10])=[O:9]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 583755ethyl 2-(2H-tetrazol-5-yl)benzoate

生成物 1

HCID 5551922-(1H-1,2,3,4-tetrazol-5-yl)benzoic acid収率 0.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Methyl 2-cyanobenzoate (0.124 moles, 20.0 g) was dissolved in 55 g tributyltinazide and heated at 85° C. for 72 hours. The solution was allowed to cool. Methanol (200 ml) and water (50 ml) were added. The solution was stirred for 1 hour. Ethyl acetate and brine were added. The organic layer was dried and evaporated. The residue was triturated 3 times with large volumes of hexane, dissolved in chloroform, and precipitated with hexane. The precipitate was filtered to yield 10.0 g of ethyl 2-(2H-tetrazol-5-yl)benzoate. The ester (6.8 moles, 1.4 g) was dissolved in 5 ml ethanol and 10 ml of 2N NaOH added and heated on a steam bath for 1 hour. The solvent was removed under vacuum. The residue was dissolved in water. The pH was adjusted to 2.0 using 2N HCl. The intermediate was extracted with ethyl acetate to yield 0.8 g of 2-(2H-tetrazol-5-yl)benzoic acid.

後処理

  1. temperatureheated on a steam bath for 1 hour
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in water
  4. extractionThe intermediate was extracted with ethyl acetate

出典と根拠

ORDレコード
ord-c4be0931149e45bf93a0766ff6fc6ef0
出典データセット
uspto-grants-1997_03
特許番号
US05612360

反応ノート

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