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

HRID 517607Notes

Reaction equation

HRID 517607 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].[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)#[N: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]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 71697662(Z)-4-((5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)methyl)benzonitrile

Procedure

The title compound 28m was prepared from compound 2 (75 mg, 0.30 mmol), p-cyanobenzyl bromide (65 mg, 0.33 mmol) and potassium carbonate (83 mg, 0.60 mmol) in a manner similar to that described for 28d in 81.5% (89 mg) yield as a light-yellow solid.

Workup

  1. customyield as a light-yellow solid

Sources & evidence

ORD record
ord-ef0e5a284547439eb199d075eee84d95
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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