Ethyl orthoformate → 1-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole

HRID 1386742ノート

反応式

HRID 1386742 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[CH:15](OCC)(OCC)OCC>CC(O)=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]2[CH:15]=[N:13][N:12]=[N:11]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 754524-Methoxybenzylamine

生成物 1

HCID 109978051-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole収率 43.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3.84 g (28.0 mmol) of (4-methoxy)benzylamine, 2.73 g (42.0 mmol) of sodium azide and 7.50 mL (45.0 mmol) triethyl orthoformate in 25 mL of HOAc was stirred at 80° C. for 20 h. The reaction was cooled and concentrated. The residue was partitioned between 100 mL of EtOAc and 100 mL of H2O and the layers were separated. The organic layer was washed with 100 mL of 2.0 N HCl, 100 mL of sat'd NaHCO3, 100 mL of sat'd NaCl, dried over MgSO4 and concentrated. Flash chromatography on 100 g of silica gel using 2:1 v/v hexanes/EtOAc, then 1:1 v/v hexanes/EtOAc as the eluant afforded 2.32 g of the title compound: 1H NMR (300 MHz) δ 3.82 (s, 3H), 5.53 (s, 2H), 6.93 (d, J=8.6, 2H), 7.27 (d, J=8.6, 2H), 8.46 (s, 1H).

後処理

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between 100 mL of EtOAc and 100 mL of H2O
  4. customthe layers were separated
  5. washThe organic layer was washed with 100 mL of 2.0 N HCl, 100 mL of sat'd NaHCO3, 100 mL of sat'd NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4f3df1f3124e413c9b4bc171c0423abb
出典データセット
uspto-grants-2001_07
特許番号
US06265434B1

反応ノート

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