Sodium Hydroxide → 2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid

HRID 2197679

반응식

HRID 2197679 반응식
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[NH2:3].[OH-].[Na+].[C:15]([CH2:18][S:19][C:20](=S)[S:21]CC(O)=O)(O)=[O:16]>O>[O:16]=[C:15]1[CH2:18][S:19][C:20](=[S:21])[N:3]1[NH:2][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 806183,5-Dithia-4-thioxo-1,7-heptanedioic acidHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)

생성물 1

HCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid수율 82.2%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a water (20 mL) solution of 2-hydrazino-benzoic acid hydrochloride (2.508 g, 13.30 mmol) was added water solution of sodium hydroxide (1.029 N, d=1.040, 26.81 g, 26.60 mmol) followed by bis(carboxymethyl)trithiocarbonate (3.006 g, 13.28 mmol). The mixture was stirred at reflux temperature for 10 h, cooled to room temperature and stirred for 50 h. The solid product was filtered off and washed on funnel successively with water (2×10 ml), ether (5 mL) and hexane (20 mL). The material was dried in a vacuum oven at 80° C. for 5 h to afford 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (2.93 g, 82%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 4.33 (1H, bs), 6.66 (1H, m), 6.90 (1H, m), 7.40 (1H, m), 7.89 (1H, m), 13.37 (1H, bs). ESI-MS: 267.0.

후처리

  1. temperatureat reflux temperature for 10 h
  2. stirringstirred for 50 h
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with water (2×10 ml), ether (5 mL) and hexane (20 mL)
  5. customThe material was dried in a vacuum oven at 80° C. for 5 h

출처 및 근거

ORD 기록
ord-03a4fd3dc4194c669f6ab9fa43acc327
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

연결된 노트

불러오는 중…