Hydrochloric Acid → (Z)-5-(4-ethoxybenzylidene)-3-(pyridin-2-ylmethyl)thiazolidine-2,4-dione

HRID 517604Notes

Reaction equation

HRID 517604 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]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]Cl.Cl.[I-].[Na+].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:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 71697659(Z)-5-(4-ethoxybenzylidene)-3-(pyridin-2-ylmethyl)thiazolidine-2,4-dione

Procedure

The title compound 28j was prepared from compound 2 (75 mg, 0.30 mmol), 2-picolyl chloride.HCl (54 mg, 0.33 mmol), sodium iodide (45 mg, 0.30 mmol) and potassium carbonate (104 mg, 0.75 mmol) in a manner similar to that described for 28d in 97.5% (99 mg) yield as a white solid.

Workup

  1. customyield as a white solid

Sources & evidence

ORD record
ord-b1508466d4fe4bc59719dd25530b7192
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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