Sodium Hydroxide → 1-methyl-5-(3-nitrophenyl)-1H-Tetrazole

HRID 896514

反応式

HRID 896514 の反応式
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1.[N-:14]=[N+:15]=[N-:16].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[OH-].[Na+]>C(#N)C>[CH3:1][N:2]1[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=2)=[N:16][N:15]=[N:14]1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 221964N-methyl-3-nitrobenzamide

生成物 1

HCID 140450781-methyl-5-(3-nitrophenyl)-1H-Tetrazole収率 18%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

N-Methyl-3-nitro-benzamide (30.0 g, 167 mmol) was dissolved in acetonitrile (835 mL), sodium azide (10.9 g, 167 mmol) was added and the mixture was cooled in an ice bath. Trifluoromethanesulfonic anhydride (29 mL, 172 mmol) was added dropwise at a rate which maintained the internal temperature below 3° C. The reaction mixture was stirred for 3.5 hours at 0° C. and then was poured into IN aqueous sodium hydroxide (100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum to 50 mL. The solution was diluted with dichloromethane and water was added to precipitate a yellow solid (18.46 g, 54%). A second crop of crystals was obtained by concentrated the filtrate in vacuo and adding it to boiling ethyl acetate. Upon cooling to 0° C., additional material (6.07 g, 18%) was isolated by filtration. 1H NMR (300 MHz, CDCl3), δ8.67 (m, 1H), 8.49 (dd, J=8, 2 Hz, 1H), 8.31 (d, J=8 Hz, 1H), 7.94 (dd, J=8, 8 Hz, 1H), 4.22 (s, 3H).

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. temperaturemaintained the internal temperature below 3° C
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum to 50 mL
  6. additionThe solution was diluted with dichloromethane and water
  7. additionwas added
  8. customto precipitate a yellow solid (18.46 g, 54%)
  9. customA second crop of crystals was obtained
  10. concentrationby concentrated the filtrate in vacuo
  11. additionadding it
  12. temperatureUpon cooling to 0° C.

出典と根拠

ORDレコード
ord-4c2b114b71084a85885f7e0a37bb4555
出典データセット
uspto-grants-2005_07
特許番号
US06919356B2

関連ノート

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