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

HRID 1713064

反応式

HRID 1713064 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, 2.38 mol), ethyl 2-mercaptoacetate (361.2 g, 3.01 mol), sodium carbonate (265 g, 2.5 mol) and EtOH (1.2 l) was heated to reflux for 4.5 h. The reaction mixture was then cooled to ambient temperature and added to water (15 l). The resulting slurry was stirred for 0.5 h then filtered. The filter cake was washed with two portions of water (2×2.5 l). The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493 g, 93%). 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, br), 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 h
  3. filtrationthen filtered
  4. washThe filter cake was washed with two portions of water (2×2.5 l)
  5. customThe solids were then dried to constant weight under vacuum at 45° C.

出典と根拠

ORDレコード
ord-754035339ba0479390b91ed3f2896832
出典データセット
uspto-grants-2010_09
特許番号
US07795256B2

関連ノート

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