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

HRID 2358848

반응식

HRID 2358848 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), 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° 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)+

후처리

  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° C.

출처 및 근거

ORD 기록
ord-130e2f275342447983a1250fac652e5c
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763729B2

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