Potassium Carbonate → (Z)-tert-butyl 4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzoate

HRID 517610Notes

Reaction equation

HRID 517610 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].Br[CH2:19][C:20]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=1.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]([CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:22][CH:21]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 71697763(Z)-tert-butyl 4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzoate

Procedure

The title compound 28p was prepared from compound 2 (75 mg, 0.30 mmol), tert-butyl 4-(bromomethyl)benzoate (106 mg, 0.39 mmol) and potassium carbonate (83 mg, 0.60 mmol) in a manner similar to that described for 28d in 96.4% (127 mg) yield as a white solid.

Workup

  1. customyield as a white solid

Sources & evidence

ORD record
ord-3855c84a5cfa404abbc4b9ed995842e9
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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