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

HRID 2112067

반응식

HRID 2112067 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 96.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)+.

후처리

  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.

출처 및 근거

ORD 기록
ord-de425d779afb41bca0ce78a338b75ca2
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521460B2

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