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

HRID 628496ノート

反応式

HRID 628496 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

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

後処理

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for fifteen minutes
  3. temperatureAfter cooling
  4. stirringwith stirring
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated saline
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationwas then concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b5566965523a41acb92f145503a67035
出典データセット
uspto-grants-2016_04
特許番号
US09314023B2

反応ノート

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