Triethylamine → HCID 46941716、化合物

HRID 468666ノート

反応式

HRID 468666 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 14046677HCID 14046677、化合物

生成物 1

HCID 46941716HCID 46941716、化合物収率 22%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d935ff208d8d442ebb1ab9b9562f0818
出典データセット
uspto-grants-2014_01
特許番号
US08624040B2

反応ノート

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