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

HRID 2112067

反応式

HRID 2112067 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 96.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-chloro-3-cyanopyridine (330 g, 2.3 mol), ethyl 2-mercaptoacetate (361.2 g, 3.0 mol), sodium carbonate (265 g, 2.5 mol) and EtOH (1.2L) was heated to reflux for 4.5 hours. The reaction mixture was cooled to ambient temperature and added to water (15L). The resultant precipitate was stirred for 30 minutes and then filtered. The filter cake was washed with two portions of water (2×2.5L) and dried to constant weight under vacuum at 45° C. 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. filtrationfiltered
  4. washThe filter cake was washed with two portions of water (2×2.5L)
  5. customdried to constant weight under vacuum at 45° C.

出典と根拠

ORDレコード
ord-de425d779afb41bca0ce78a338b75ca2
出典データセット
uspto-grants-2009_04
特許番号
US07521460B2

関連ノート

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