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

HRID 331674ノート

反応式

HRID 331674 の反応式
[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

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178509299HCID 178509299、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5bdd2ca5bff045c2a5fa2e817696fe1a
出典データセット
uspto-grants-2014_11
特許番号
US08877786B2

反応ノート

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