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

HRID 892225노트

반응식

HRID 892225 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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 conc. hydrochloric acid. The precipitated product was slurried with ice cooling for 15 minutes, filtered, water washed and dried under vacuo at 50° C. to afford the sub-title compound (4.1 g, 43%) as an off-white solid. Mpt 206–207° C. δ (CDCl3): 1.25 (3H, t), 1.39 (3H, t), (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).

후처리

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

출처 및 근거

ORD 기록
ord-6f22e421cc58438da081cce661563616
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005520B2

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