Hydrochloric Acid → 1-Oxo-1H-isothiochromene-3-carboxylic acid

HRID 259260Notes

Reaction equation

HRID 259260 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH:6]=[C:7]1[S:11]C(=S)N[C:8]1=[O:13])([OH:3])=O.[OH-:18].[Na+].Cl>O>[C:1]1([C:4]2[C:5](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[C:7]([C:8]([OH:18])=[O:13])[S:11]1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28263832-[(4-Oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoic acid

Product 1

HCID 3455601-Oxo-1H-isothiochromene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5- (o-carboxybenzylidene) rhodanine (4.68g.) and sodium hydroxide (5.0g.) in water (40ml.) was heated under reflux for 30 minutes, cooled and poured into 5N hydrochloric acid (250ml.). Filtration and recrystallisation from ethanol-water gave the product as a white solid, mp. 260.5° - 261° (lit mp. 261°-3°), (Found: C, 58.10; H, 2.92; S, 15.41. C10H6SO3 requires C, 58.24; H, 2.93; S, 15.55).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. filtrationFiltration and recrystallisation from ethanol-water

Sources & evidence

ORD record
ord-b9961e6d747c406e892ec897ca94cfdc
Source dataset
uspto-grants-1977_07
Patent number
US04036964

Reaction notes

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