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

HRID 2197679

反応式

HRID 2197679 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-03a4fd3dc4194c669f6ab9fa43acc327
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

関連ノート

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