3-Aminobenzoic Acid → 3-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzoic acid

HRID 2197688Notes

Reaction equation

HRID 2197688 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]([CH2:14][S:15][C:16](=S)[S:17]CC(O)=O)(O)=[O:12].[OH-].[Na+]>>[O:12]=[C:11]1[CH2:14][S:15][C:16](=[S:17])[N:1]1[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 14798Sodium HydroxideHCID 806183,5-Dithia-4-thioxo-1,7-heptanedioic acid

Product 1

HCID 3028893-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzoic acidYield 82.1%

Procedure

3-amino-benzoic acid (6.00 g, 43.77 mmol), bis(carboxymethyl)trithiocarbonate (10.2 g, 45.09 mmol) in 1.029 N aqueous sodium hydroxide (44.5 g, 44.06 mmol) was heated at 100° C. for 16 h. The reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed successively with 3N aqueous HCl (3×20 mL), water (3×20 mL), ethanol (2×20 mL) and dried in vacuum oven at 60° C. for 2 h to obtain 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-benzoic acid (9.10 g, 82%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 4.34 (2H, s), 7.52-7.55 (1H, m), 7.67 (1H, t, J=8 Hz), 7.87 (1H, t, J=2 Hz), 8.02-8.05 (1H, dt, J=1.2 & 2.8 Hz); ESI-MS: 253.30.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed successively with 3N aqueous HCl (3×20 mL), water (3×20 mL), ethanol (2×20 mL)
  3. customdried in vacuum oven at 60° C. for 2 h

Sources & evidence

ORD record
ord-667f1617873d4482843988e4e999fbaa
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Reaction notes

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