Sodium Chloride → 5-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole

HRID 747183ノート

反応式

HRID 747183 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13]OS(C)(=O)=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:19]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:12]1)=[N+:20]=[N-:21]

参加物

5

反応物 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 18698757[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl methanesulfonate

生成物 1

HCID 179544685-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole収率 112.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Methanesulfonic acid 3-(4-bromo-phenyl)-4,5-dihydro-isoxazol-5-ylmethyl ester (55 g, 164.2 mmol) was added to dimethyl formamide (200 ml) followed by addition of sodium azide (21.4 g, 328.4 mmol). The mixture was heated to 75° C. for six hours and then added to aqueous sodium chloride (300 ml) followed by extraction with gethyl acetate (3×300 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to yield the desired product (52 g).

後処理

  1. extractionfollowed by extraction with gethyl acetate (3×300 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e8cab888258b4224a137730ce68e6483
出典データセット
uspto-grants-2008_07
特許番号
US07396847B2

反応ノート

読み込み中…