Cesium carbonate → 1-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine

HRID 331674노트

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HRID 331674 반응식
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:3]2[C:2]([NH2:1])=[N:6][N:5]=[N:4]2)=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178509299HCID 178509299, 화합물

생성물 1

HCID 240234561-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine수율 17.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a suspension of 5-amino-1H-tetrazole (1.50 g, 17.6 mmol) in DMF (30 mL) were added Cs2CO3 (8.62 g, 26.4 mmol) and PMBCl (2.90 g, 18.5 mmol). After stirred at 60° C. for 3 hours, the reaction mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was diluted with DCM and the resulted precipitate was collected by filtration to give 1-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine (0.625 g). 1H NMR (400 MHz, DMSO-d6) δ 3.73 (s, 3H), 5.27 (s, 2H), 6.78 (s, 2H), 6.92 (d, 2H, J=8.8 Hz), 7.21 (d, 2H, J=8.8 Hz).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with DCM
  6. filtrationthe resulted precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-5bdd2ca5bff045c2a5fa2e817696fe1a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877786B2

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