Sodium Carbonate → Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate

HRID 1184817ノート

反応式

HRID 1184817 の反応式
Cl[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16]([O:18][C:19](=[O:22])[CH2:20][SH:21])[CH3:17]>C(O)C>[NH2:9][C:8]1[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[S:21][C:20]=1[C:19]([O:18][CH2:16][CH3:17])=[O:22]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 2924653-Chloropyrazine-2-carbonitrile

生成物 1

HCID 2820821Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate収率 68.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5 h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5%). 1H-NMR (400 MHz, CDCl3) 1.42 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. customQuenched with water (1.5 L)
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. dissolutionThe residue was dissolved in diethyl ether
  7. filtrationa black precipitate was filtrated off
  8. customEther was evaporated

出典と根拠

ORDレコード
ord-d6aa3e1b4e374f28ba77786de6b250da
出典データセット
uspto-grants-2014_03
特許番号
US08669256B2

反応ノート

読み込み中…