3-Furoic acid → HCID 65214101, compound

HRID 1259857Notes

Reaction equation

HRID 1259857 reaction equation
S(Cl)(Cl)=O.[O:5]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=O)=[CH:6]1.[NH2:13][NH:14][C:15]([NH2:17])=[S:16].C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl>[O:5]1[CH:9]=[CH:8][C:7]([C:10]([NH:13][NH:14][C:15]([NH2:17])=[S:16])=[O:12])=[CH:6]1

Participants

7

Reactant 4

HCID 102683-Furoic acidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 2723789Thiosemicarbazide

Product 1

HCID 65214101HCID 65214101, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (3 mL) was added to a dichloromethane (10 mL) solution of 3-furancarboxylic acid (2.50 g, 22.3 mmol) under ice cooling, and the mixture was heated to reflux for 2 hours. The solvent was distilled off. After that, the residue was concentrated by the addition of toluene and added to a THF (50 mL) solution of thiosemicarbazide (4.47 g, 49.1 mmol) under ice cooling, and the mixture was stirred overnight at room temperature. To the reaction solution, a saturated aqueous solution of sodium bicarbonate was added. The mixture was subjected to extraction with ethyl acetate and dried over anhydrous sodium sulfate, and then, the solvent was distilled off to obtain 1-(3-furoyl)thiosemicarbazide (3.03 g, 16.4 mmol) (yield: 74%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. distillationThe solvent was distilled off
  4. concentrationAfter that, the residue was concentrated by the addition of toluene
  5. extractionThe mixture was subjected to extraction with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5285d8878bb24f7a8d2147cd9df7de96
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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