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

HRID 637169노트

반응식

HRID 637169 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-33257545030f42228177537b8f9ec6b5
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194406B1

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