2-(3,4-Dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole → 3-Nitro-5-[5-(2-trifluoromethyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diol

HRID 61982ノート

反応式

HRID 61982 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[O:15][C:16]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:18]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C>Br.C(O)(=O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:14]2[O:15][C:16]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][N:18]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

参加物

4

反応物 1

HCID 670370412-(3,4-Dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole

生成物 1

HCID 1363887153-Nitro-5-[5-(2-trifluoromethyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diol

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 260Hydrogen Bromide溶媒2 回

反応条件

温度
140 °C

実験手順

A suspension of 2-(3,4-dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole (0.289 g, 0.73 mmol) in a mixture of 48% hydrobromic acid (5 mL) and 30% hydrogen bromide in acetic acid (5 mL) was heated at 140° C. overnight and then allowed to cool to room temperature. After evaporation to dryness under reduced pressure, toluene (10 mL) was added to the residue and re-evaporated under reduced pressure. The resulting solid was recrystallised from isopropanol to give 3-nitro-5-[5-(2-trifluoromethyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diol as a yellow solid, 0.183 g, (68%).

後処理

  1. temperatureto cool to room temperature
  2. customAfter evaporation to dryness under reduced pressure, toluene (10 mL)
  3. additionwas added to the residue
  4. customre-evaporated under reduced pressure
  5. customThe resulting solid was recrystallised from isopropanol

出典と根拠

ORDレコード
ord-31e89084da2140fc83b2bfb64f8a2aa8
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

反応ノート

読み込み中…