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

HRID 2197679

Reaction equation

HRID 2197679 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-03a4fd3dc4194c669f6ab9fa43acc327
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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