Water → (1-methyl-1H-tetrazol-5-yl)(phenyl)methanone

HRID 42716

반응식

HRID 42716 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N+:11]#[C-:12].[N-:13]=[N+:14]=[N-:15].[Na+].O>C(#N)C.C(OCC)(=O)C>[CH3:12][N:11]1[C:10]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:15][N:14]=[N:13]1

참가 물질

7

반응물 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 11646Methyl isocyanideHCID 33557Sodium Azide

생성물 1

HCID 12331986(1-methyl-1H-tetrazol-5-yl)(phenyl)methanone수율 65.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

At room temperature, 10 g of benzoyl chloride (71 mmol) were admixed with 3.7 g (92 mmol) of methyl isocyanide. The mixture was then heated at 60° C. for 2 hours. The mixture was admixed with 25 ml of acetonitrile and cooled to 0° C. This reaction mixture was added to 4.6 g of sodium azide (71 mmol) in 25 ml of acetonitrile at 0° C. The mixture was then heated to 60° C. to 65° C. and stirred at this temperature for 16 hours. At room temperature, 100 ml of water and 100 ml of ethyl acetate were added to the mixture. The organic phase was separated off and the aqueous phase was extracted with 100 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and the solvent was removed in vacuo. The crude product could be recrystallized from 20 ml of isopropanol, giving 8.7 g of 1-methyl-5-benzoyltetrazole (purity 99.4%). This corresponds to a yield of 65%, based on the acid chloride used.

후처리

  1. customAt room temperature
  2. temperaturecooled to 0° C
  3. temperatureThe mixture was then heated to 60° C. to 65° C.
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted with 100 ml of ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. customthe solvent was removed in vacuo
  8. customThe crude product could be recrystallized from 20 ml of isopropanol

출처 및 근거

ORD 기록
ord-70f69eb9422d4901ac5aadc1c16f77a7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536211B2

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