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

HRID 517606Notes

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

Participants

Reactant 6

HCID 313Hydrochloric Acid

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 745714-(Chloromethyl)pyridine

HCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Product 1

HCID 71697661(Z)-5-(4-ethoxybenzylidene)-3-(pyridin-4-ylmethyl)thiazolidine-2,4-dione

Procedure

The title compound 28l was prepared from compound 2 (75 mg, 0.30 mmol), 4-picolyl chloride.HCl (54 mg, 0.33 mmol), sodium iodide (45 mg, 0.30 mmol) and potassium carbonate (124 mg, 0.90 mmol) in a manner similar to that described for 28d in 96.1% (98 mg) yield as a white solid.

Workup

customyield as a white solid

Sources & evidence

ORD record: ord-05e3eab09f0f4054b19cf3a4cea85607
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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