Triethylamine → HCID 46941716, 화합물

HRID 468666노트

반응식

HRID 468666 반응식
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[C:22](=O)[CH3:23]>C(#N)C>[CH3:23][C:22]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[S:1][C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 14046677HCID 14046677, 화합물

생성물 1

HCID 46941716HCID 46941716, 화합물수율 22%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of ethyl 2-mercaptoacetate (5.52 g, 0.046 mol) and triethylamine (5.52 g, 0.055 mol) in acetonitrile (100 mL) at room temperature was added 1-(4-chloropyridin-3-yl)ethanone (6.5 g, 0.042 mol). The reaction mixture was heated at reflux for 18 hours. Upon cooling to room temperature, the solvent was evaporated and the residue obtained partitioned between ethyl acetate and water. The organic layer was dried over anhydrous NaHSO4, filtered and concentrated. The oily residue was passed through a pad of silica (ethyl acetate/hexane: 5/1) to afford ethyl 3-methylthieno[3,2-c]pyridine-2-carboxylate (1.6 g, 22%). LCMS (FA) ES+ 222; 1H NMR (400 MHz, CDCl3) δ 9.10 (s, 1H), 8.50 (d, J=5.6 Hz, 1H), 7.98 (d, J=17.6 Hz, 1H), 4.37 (d, J=7.2 Hz, 2H), 3.58 (t, J=5.9 Hz, 2H), 1.38 (d, J=7.2 Hz, 3H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent was evaporated
  4. customthe residue obtained
  5. custompartitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over anhydrous NaHSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d935ff208d8d442ebb1ab9b9562f0818
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624040B2

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