Ethylamine → 5-{[3-(Ethylamino)-4-nitrophenyl]methylidene}-1,3-thiazolidine-2,4-dione

HRID 2261090Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].[CH2:19]([NH2:21])[CH3:20]>COCCOC>[CH2:19]([NH:21][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12])[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

5-(3-Fluoro-4-nitro-benzylidene)-thiazolidine-2,4-dione (200 mg, 0.75 mmol, 1 eq.), was dissolved in DME (6 mL) and TEA (208 μL, 1.5 mmol, 2 eq.) and a solution of ethylamine (2 eq.) was added. The reaction mixture was shaken at 60° C. over night. The solvent was removed in vacuo and residue dissolved in ethyl acetate and washed with 10% ammonium chloride aqueous solution. The organic layer was dried on Na2SO4 and the solvent evaporated to give the corresponding aniline derivative as either red oil, which was used for the next step without further purification.

Workup

customThe solvent was removed in vacuo and residue
dissolutiondissolved in ethyl acetate
washwashed with 10% ammonium chloride aqueous solution
customThe organic layer was dried on Na2SO4
customthe solvent evaporated

Sources & evidence

ORD record: ord-196f00412982452d81ee7473a9441538
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846925B2

Reaction notes

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