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

HRID 896514

반응식

HRID 896514 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-4c2b114b71084a85885f7e0a37bb4555
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919356B2

연결된 노트

불러오는 중…