Hydrochloric Acid → 1-(2-Methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one

HRID 1048619ノート

反応式

HRID 1048619 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]=[C:17]=[O:18])[C:11]=1[CH3:19].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH3:19][C:11]1[C:10]([Br:9])=[CH:15][CH:14]=[CH:13][C:12]=1[N:16]1[C:17](=[O:18])[NH:7][N:6]=[N:5]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium NitriteHCID 655423311-Bromo-3-isocyanato-2-methyl-benzene

生成物 1

HCID 1366461861-(2-Methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one収率 86.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Under ice-cooling, to N,N-dimethylformamide 220 mL was added anhydrous aluminum chloride 19.7 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 9.6 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-bromo-3-isocyanato-2-methylbenzene 30.3 g and the resulting mixtures were heated at 80° C. for five hours. After cooling the mixtures, to a mixture of sodium nitrite 33 g, water 2 L and ice 500 g was added the reaction solutions with stirring. The mixtures were acidified with 10% hydrochloric acid and were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazole-5-one 31.4 g.

後処理

  1. stirringthe resulting mixtures were stirred for fifteen minutes
  2. temperatureAfter cooling the mixtures
  3. additionwas added the reaction solutions
  4. stirringwith stirring
  5. extractionwere extracted with ethyl acetate
  6. washThe organic layers were washed with water and saturated saline
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. concentrationwere then concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d442d0aec58746beb02aa3cf9068cbe7
出典データセット
uspto-grants-2016_07
特許番号
US09380782B2

反応ノート

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