Tributylphosphine → 5-{4-[2-(3-Quinolylmethyleneaminooxy)ethoxy]benzyl}-3-tritylthiazolidine-2,4-dione

HRID 1941630Notes

Reaction equation

HRID 1941630 reaction equation
N(C(N1CCNCC1)=O)=NC(N1CCNCC1)=O.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([CH:29]=[N:30][O:31][CH2:32][CH2:33][OH:34])[CH:20]=1.O[C:36]1[CH:68]=[CH:67][C:39]([CH2:40][CH:41]2[S:45][C:44](=[O:46])[N:43]([C:47]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]2=[O:66])=[CH:38][CH:37]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.O1CCCC1>[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([CH:29]=[N:30][O:31][CH2:32][CH2:33][O:34][C:36]2[CH:68]=[CH:67][C:39]([CH2:40][CH:41]3[S:45][C:44](=[O:46])[N:43]([C:47]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]3=[O:66])=[CH:38][CH:37]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 537495822-(3-Quinolylmethyleneaminooxy)ethanolHCID 544718201,1'-(Azodicarbonyl)dipiperazine

Product 1

HCID 738479795-{4-[2-(3-Quinolylmethyleneaminooxy)ethoxy]benzyl}-3-tritylthiazolidine-2,4-dioneYield 92.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.73 g of 1,1'-(azodicarbonyl)dipiperazine in 10 ml of toluene was added dropwise at room temperature to a suspension of 0.60 g of 2-(3-quinolylmethyleneaminooxy) ethanol (prepared as described in Preparation 3), 1.10 g of 5-(4-hydroxy-benzyl)-3-tritylthiazolidine-2,4-dione and 0.72 ml of tributylphosphine in 30 ml of tetrahydrofuran, and the resulting mixture was stirred for 16 hours. At the end of this time, the reaction product was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.45 g of the title compound as a crystalline powder, melting at 127°-130° C.

Workup

  1. customAt the end of this time, the reaction product was purified by column chromatography through silica gel
  2. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-b7ed13fea3d14bcb9d96597d5518110a
Source dataset
uspto-grants-1997_12
Patent number
US05703096

Reaction notes

Loading…