Triphenylphosphine → 5-(4-{2-[1-(4-Biphenylyl)ethylideneaminooxy]ethoxy}benzyl)-3-tritylthiazolidine-2,4-dione

HRID 1741305Notes

Reaction equation

HRID 1741305 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7](=[N:9][O:10][CH2:11][CH2:12][OH:13])[CH3:8])=[CH:3][CH:2]=1.O[C:21]1[CH:53]=[CH:52][C:24]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[N:28]([C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]2=[O:51])=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7](=[N:9][O:10][CH2:11][CH2:12][O:13][C:21]2[CH:53]=[CH:52][C:24]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[N:28]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]3=[O:51])=[CH:23][CH:22]=2)[CH3:8])=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 544003492-[1-(4-Biphenylyl)ethylideneaminooxy]ethanol

Product 1

HCID 867518015-(4-{2-[1-(4-Biphenylyl)ethylideneaminooxy]ethoxy}benzyl)-3-tritylthiazolidine-2,4-dioneYield 71.5%

Procedure

Following a procedure similar to that described in Example 1(a), but using 170 mg of 2-[1-(4-biphenylyl)-ethylideneaminooxy]ethanol (prepared as described in Preparation 15), 238 mg of 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione, 175 mg of triphenylphosphine and 116 mg of diethyl azodicarboxylate, 257 mg of the title compound were obtained as a crystalline powder, melting at 145° C.

Sources & evidence

ORD record
ord-84d6e88a3c9c41269397b16ea3e58b4f
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

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