Sodium ethoxide → Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

HRID 1831478ノート

反応式

HRID 1831478 の反応式
Cl[C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-:24][CH2:25][CH3:26].[Na+]>C(O)C>[CH2:25]([O:24][C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:26]

参加物

4

反応物 2

HCID 2723922Sodium ethoxideHCID 22052238Ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

生成物 1

HCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate収率 34%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

A solution of ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (36.1 g, 0.1 mol) in ethanol (180 mL) was cooled to 10° C. with stirring. Sodium ethoxide (10.2 g, 0.15 mol) was added portionwise keeping the temperature below 20° C. The reaction mixture was then stirred at ambient temperature for 18 hours. The precipitate was filtered off and water (180 mL) added to the filtrate. The filtrate was then heated to 40° C. for 1 hour. Ethanol (180 mL) was then distilled off at ambient pressure and the remaining aqueous solution allowed to cool to ambient temperature. The precipitated product was then filtered off, washed with water and dried under vacuo at 50° C. to afford the title compound (12.6 g, 34%) as a light brown solid. M.p. 66–68° C. δ (CDCl3): 1.04 (3H, t), 1.39 (3H, t), 1.45 (3H, t), 2.41 (2H, q), 2.52 (4H, m), 3.08 (4H, m), 4.38 (2H, q), 2.57 (2H, q), 8.38 (1H, d), 8.61 (1H, d). m/z (Found: 372 [M+H]+, 100%. C16H26N3O5S requires 372.46).

後処理

  1. customthe temperature below 20° C
  2. stirringThe reaction mixture was then stirred at ambient temperature for 18 hours
  3. filtrationThe precipitate was filtered off
  4. additionwater (180 mL) added to the filtrate
  5. distillationEthanol (180 mL) was then distilled off at ambient pressure
  6. temperatureto cool to ambient temperature
  7. filtrationThe precipitated product was then filtered off
  8. washwashed with water
  9. customdried under vacuo at 50° C.

出典と根拠

ORDレコード
ord-4d564c638b9e4344b1e26db7c9e833d5
出典データセット
uspto-grants-2006_06
特許番号
US07067660B2

反応ノート

読み込み中…