Hydrochloric Acid → HCID 73993438, compound

HRID 1581651Notes

Reaction equation

HRID 1581651 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:5][C:4]=1[N+:17]([O-])=O.C(O)C.Cl.C(=O)([O-])O.[Na+]>O>[NH2:17][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 2850570HCID 2850570, compound

Product 1

HCID 73993438HCID 73993438, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-[(4-Methoxy-3-nitrophenyl)methylidene]thiazolidine-2,4-dione (841 mg, 3.00 mmol), ethanol (20 mL) and concentrated hydrochloric acid (10 mL) were mixed, and tin chloride(II) dihydrate (2.26 g, 9.01 mmol) was added little by little at room temperature under stirring. After stirring for 8 hours at room temperature, the reaction mixture was poured into water and neutralized with saturated aqueous sodium hydrogencarbonate, which was extracted with ethyl acetate. The extracted solution was washed with water, then dried over anhydrous sodium sulfate and concentrated to obtain 641 mg (85%) of the title compound as yellowish orange powder.

Workup

  1. stirringAfter stirring for 8 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe extracted solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e91c34209f3b47e9ab97339d739b7eb3
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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