Diethylamine → 5-(5-Pyridin-3-yl-pent-4-ynyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

HRID 395387Notes

Reaction equation

HRID 395387 reaction equation
[CH2:1]([C:6]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12])[CH2:2][CH2:3][C:4]#[CH:5].[CH2:23](O)[CH2:24][CH2:25][C:26]#[CH:27].C([NH:31]CC)C>ClCCl.[Cu]I>[N:31]1[CH:27]=[CH:26][CH:25]=[C:24]([C:5]#[C:4][CH2:3][CH2:2][CH2:1][C:6]2([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[S:10][C:9](=[O:11])[NH:8][C:7]2=[O:12])[CH:23]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 793464-Pentyn-1-olHCID 226780015-Pent-4-ynyl-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

Product 1

HCID 226780195-(5-Pyridin-3-yl-pent-4-ynyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-pent-4-ynyl-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione(1.0 mmol), 4-pentyn-1-ol (1.0 mmol), bistriphenylphosphine(Pd II) chloride (0.20 mmol), and copper(I) iodide (0.10 mmol) in 50 ml of diethylamine was stirred under nitrogen for three days. This was diluted with dichloromethane and the product was purified by chromatography to give the title compound as a light beige solid, mp 173-176° C., THEORY: C, 57.95, H, 4.38 N, 6.76. FOUND: C, 57.68, H, 4.35, N, 6.70.

Workup

  1. customthe product was purified by chromatography

Sources & evidence

ORD record
ord-2f139a37e05d4621b09b46b879def906
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Reaction notes

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