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

HRID 517605Notes

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]=[C:20]([CH2:24]Cl)[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:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=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 183583-(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 71697660(Z)-5-(4-ethoxybenzylidene)-3-(pyridin-3-ylmethyl)thiazolidine-2,4-dione

Procedure

The title compound 28k was prepared from compound 2 (75 mg, 0.30 mmol), 3-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 93.1% (95 mg) yield as a white solid.

Workup

customyield as a white solid

Sources & evidence

ORD record: ord-2c4c73fc00254f39b1240ab5a2e91a03
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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