Pyridine → 1-Benzothiophene-5-carbonitrile

HRID 883607ノート

反応式

HRID 883607 の反応式
[C:1]([Cu])#[N:2].Br[C:5]1[CH:13]=[CH:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=1.N1C=CC=CC=1.C(N)CN>CN(C=O)C>[S:9]1[CH:10]=[CH:11][C:7]2[CH:6]=[C:5]([C:1]#[N:2])[CH:13]=[CH:12][C:8]1=2

参加物

6

反応物 4

HCID 1049PyridineHCID 3301EthylenediamineHCID 27765785-Bromo-1-benzothiopheneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 27954521-Benzothiophene-5-carbonitrile収率 92.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of CuCN (86 g, 960 mmol), 5-bromobenzo[b]thiophene (157 g, 723 mmol), pyridine (80 mL) and DMF (1400 mL) was heated at reflux for 14 h. After cooled to 80° C., the reaction mixture was poured into a cold aqueous solution of ethylenediamine (400 mL in 2 L water) cooled by an icebath. The product was extracted with ether (2×1.5 L). The ether layer was washed with brine (1 L), dried (Na2SO4), and concentrated. The residue was recrystallized from CHCl3/Hexanes (50 mL/2000 mL) to give benzo[b]thiophene-5-carbonitrile (106 g, 90%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.15 (s, 1H), 7.97 (d, J=8.3 Hz, 1H), 7.61 (d, J=5.4 Hz, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.41 (d, J=5.4 Hz, 1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 14 h
  3. temperaturecooled by an icebath
  4. extractionThe product was extracted with ether (2×1.5 L)
  5. washThe ether layer was washed with brine (1 L)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from CHCl3/Hexanes (50 mL/2000 mL)

出典と根拠

ORDレコード
ord-ecdec77910bc4409941c5028f2a1cec3
出典データセット
uspto-grants-2012_08
特許番号
US08236796B2

反応ノート

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