Potassium Carbonate → 5-{[4-Amino-3-(ethylamino)phenyl]methylidene}-1,3-thiazolidine-2,4-dione

HRID 2261091Notes

Reaction equation

HRID 2261091 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[CH:7]=[C:8]1[S:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:18])[CH:7]=[C:8]1[S:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 713782695-{[3-(Ethylamino)-4-nitrophenyl]methylidene}-1,3-thiazolidine-2,4-dione

Product 1

HCID 713782715-{[4-Amino-3-(ethylamino)phenyl]methylidene}-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(3-Ethylamino-4-nitro-benzylidene)-thiazolidine-2,4-dione in THF, a solution of sodium hydrosulfite (3 eq.) in water was slowly added followed by an aqueous solution of K2CO3. The reaction mixture was refluxed over night. THF was removed in vacuo and residue extracted with ethyl acetate The organic layer was dried on Na2SO4 and the solvent evaporated to give the corresponding aniline derivative, which was used without any further purification.

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. customTHF was removed in vacuo and residue
  3. extractionextracted with ethyl acetate The organic layer
  4. customwas dried on Na2SO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-f5cc876c00a34a2caac578bce01c8532
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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