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

HRID 1956902Notes

Reaction equation

HRID 1956902 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[N:8][O:9][CH2:10][CH2:11][OH:12])=[CH:3][CH:2]=1.O[C:14]1[CH:46]=[CH:45][C:17]([CH2:18][CH:19]2[S:23][C:22](=[O:24])[N:21]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]2=[O:44])=[CH:16][CH:15]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCNCC1)=O)=NC(N1CCNCC1)=O>>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[N:8][O:9][CH2:10][CH2:11][O:12][C:14]2[CH:46]=[CH:45][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[N:21]([C:25]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]3=[O:44])=[CH:16][CH:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 541439302-(4-Pyridylmethyleneaminooxy)ethanolHCID 544718201,1'-(Azodicarbonyl)dipiperazine

Product 1

HCID 738479885-{4-[2-(4-Pyridylmethyleneaminooxy)ethoxy]benzyl}-3-tritylthiazolidine-2,4-dioneYield 41.7%

Procedure

Following a procedure similar to that described in Example 3(a), but using 0.88 g of 2-(4-pyridylmethyleneaminooxy)ethanol (prepared as described in Preparation 6), 2.00 g of 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione, 1.32 ml of tributylphosphine and 1.23 g of 1,1'-(azodicarbonyl)dipiperazine, 1.10 g of the title compound were obtained as a foam-like solid.

Sources & evidence

ORD record
ord-e7b785cd14664cb1a15a2b0618ff9694
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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