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

HRID 1713064

반응식

HRID 1713064 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)+.

후처리

  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.

출처 및 근거

ORD 기록
ord-754035339ba0479390b91ed3f2896832
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795256B2

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