Acetic Acid → 2-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1868293ノート

反応式

HRID 1868293 の反応式
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([C:11]#[N:12])=[CH:4][NH:3]1.C(O)(=O)C.[I:17]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[I:17][C:9]1[S:10][C:6]2[C:5]([C:11]#[N:12])=[CH:4][NH:3][C:2](=[O:1])[C:7]=2[CH:8]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 184465784-Oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

生成物 1

HCID 184465252-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile収率 84.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To 4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile 24 (5 g, 28.4 mmol) in a 1:1 solution of acetic acid and DMF (18.4 mL) was added N-iodosuccinimide (12.8 g, 56.8 mmol). The reaction was warmed to 80° C. and stirred for 21 h. The reaction was diluted 10 fold with water and neutralized with aqueous sodium bicarbonate. The precipitate was filtered, washed with water and dried to provide 7.27 g of 25. 1H NMR (400 MHz, d6-DMSO) δ 12.45 (s, 1H), 8.25 (d, J=5 Hz, 1H), 7.77 (s, 1H).

後処理

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

出典と根拠

ORDレコード
ord-383d1c5e9262487e8e19ae0e92535074
出典データセット
uspto-grants-2009_12
特許番号
US07635695B2

反応ノート

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