Ethyl orthoformate → methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate

HRID 323423ノート

反応式

HRID 323423 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:13]=[N:25][N:24]=[N:23]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 15049977Methyl 5-Amino-2-methylbenzoate

生成物 1

HCID 18464615methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70° C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

後処理

  1. waitAfter 2 hours
  2. temperaturecool the reaction mixture to ambient temperature
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with water
  6. customdry

出典と根拠

ORDレコード
ord-3fd9bddb88054470a808b1d78fa5196b
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

反応ノート

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