Sodium Hydroxide → 2-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acid

HRID 1700138ノート

反応式

HRID 1700138 の反応式
[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

生成物 1

HCID 46689282-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acid収率 43.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (10.2 g, 0.0275 mol) was dissolved in toluene (50 mL) and a solution of sodium hydroxide (1.1 g, 0.0275 mol) in water (20 mL) added to it. This two phase mixture was then stirred vigorously at ambient temperature overnight. The aqueous phase was separated off and adjusted to pH=5.6 by addition of c. hydrochloric acid. The precipitated product was slurried with ice cooling for 15minutes, filtered, water washed and dried under vacuo at 50° C. to afford the title compound (4.1 g, 43%) as an off-white solid. Mpt 206-207° C. d (CDCl3): 1.25 (3H, t), 1.39 (3H,t), 2.82 (2H, q), 3.03 (4H, m), 3.25 (4H, m), 4.50 (2H, q), 8.25 (1H, d), 8.56 (1H, d). m/z (Found:344 [M+H]+, 100%. C14H22N3O5S requires 344.38).

後処理

  1. customThe aqueous phase was separated off
  2. additionadjusted to pH=5.6 by addition of c
  3. waitThe precipitated product was slurried with ice cooling for 15minutes
  4. filtrationfiltered
  5. washwater washed
  6. customdried under vacuo at 50° C.

出典と根拠

ORDレコード
ord-a907806906df452d88ed068a75cd0cbc
出典データセット
uspto-grants-2002_02
特許番号
US06350751B1

反応ノート

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