Benzyl Bromide → (Z)-3-benzyl-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517603Notes

Reaction equation

HRID 517603 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].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OC1C=CC(/C=C2/C(=O)N(CCC)C(=O)S/2)=CC=1)C>>[CH2:18]([N:11]1[C:10](=[O:15])/[C:9](=[CH:8]/[C:7]2[CH:16]=[CH:17][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)/[S:13][C:12]1=[O:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 49886692(Z)-3-benzyl-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Procedure

The title compound 28i was prepared from compound 2 (75 mg, 0.30 mmol), benzyl bromide (39 μL, 0.33 mmol) and potassium carbonate (83 mg, 0.60 mmol) in a manner similar to that described for 28d in 99.6% (101 mg) yield as a white solid.

Workup

  1. customyield as a white solid

Sources & evidence

ORD record
ord-6e375dfc74c245068f00c1b7ee4c8c45
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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