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

HRID 1956901Notes

Reaction equation

HRID 1956901 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:8][O:9][CH2:10][CH2:11][OH:12])[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(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=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][CH:4]=[C:3]([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])[NH:21][C:20]3=[O:44])=[CH:16][CH:15]=2)[CH:2]=1

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 540400992-(3-Pyridylmethyleneaminooxy)ethanolHCID 544718201,1'-(Azodicarbonyl)dipiperazine

Product 1

HCID 738479875-{4-[2-(3-Pyridylmethyleneaminooxy)ethoxy]benzyl}-thiazolidine-2,4-dioneYield 85.9%

Procedure

Following a procedure similar to that described in Example 3(a), but using 0.90 g of 2-(3-pyridylmethyleneaminooxy)ethanol (prepared as described in Preparation 5), 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, 1.37 g of the title compound were obtained as a crystalline powder, melting at 155°-157° C.

Sources & evidence

ORD record
ord-cf556e3a6cdb434a8a664dc54e09f303
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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