Potassium Carbonate → (Z)-5-(4-ethoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione

HRID 517608Notes

Reaction equation

HRID 517608 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].C(OC1C=CC(/C=C2/C(=O)N(CCC)C(=O)S/2)=CC=1)C>>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[N:11]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 1498888(Z)-5-(4-ethoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione

Procedure

The title compound 28n was prepared from compound 2 (150 mg, 0.60 mmol), p-nitrobenzyl bromide (143 mg, 0.66 mmol) and potassium carbonate (166 mg, 1.20 mmol) in a manner similar to that described for 28d in 99.5% (229 mg) yield as a white solid.

Workup

  1. customyield as a white solid

Sources & evidence

ORD record
ord-ce7a9981e6bd4991afa92429fe8a4fab
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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