Ethanol → Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

HRID 347904

反応式

HRID 347904 の反応式
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[SH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].CCO>O>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

6

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 810792-Chloronicotinonitrile

生成物 1

HCID 738459Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate収率 93.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-chloro-3-cyanopyridine (330 g), ethyl 2-mercaptoacetate (361.2 g), sodium carbonate (265 g) and EtOH (1.2 L) was heated to reflux for 4.5 hours. It was then cooled to ambient temperature, added to water (10 L) and the addition was washed in with water (5 L). The resulting slurry was stirred for 30 minutes and then it was filtered. The filter cake was washed with two portions of water (2×2.5 L) and dried at the pump. The solids were then dried to constant weight under vacuum at 45° to yield the title compound as a brown solid (493.1 g, 93.2%). δH (CDCl3) 8.68 (1H, dd, J 4.7, 1.2 Hz), 7.93 (1H, dd, J 8.5, 1.2 Hz), 7.29 (1H, dd, J 8.5, 4.7 Hz), 5.90 (2H, b), 4.38 (2H, q, J 7.0 Hz), 1.40 (3H, t, J 7.0 Hz). LCMS RT 2.9 minutes, 223 (M+H)+

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. additionthe addition
  4. washwas washed in with water (5 L)
  5. filtrationit was filtered
  6. washThe filter cake was washed with two portions of water (2×2.5 L)
  7. customdried at the pump
  8. customThe solids were then dried to constant weight under vacuum at 45°

出典と根拠

ORDレコード
ord-93162a166d40405db2cbce305f16bb2d
出典データセット
uspto-grants-2007_02
特許番号
US07176215B2

関連ノート

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