Triphenylphosphine → 3-(2,4-Diethoxybenzyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

HRID 395393Notes

Reaction equation

[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:18]([O:20][C:21]1[CH:28]=[C:27]([O:29][CH2:30][CH3:31])[CH:26]=[CH:25][C:22]=1[CH2:23]O)[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>>[CH2:18]([O:20][C:21]1[CH:28]=[C:27]([O:29][CH2:30][CH3:31])[CH:26]=[CH:25][C:22]=1[CH2:23][N:12]1[C:11](=[O:16])[CH:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[S:14][C:13]1=[O:15])[CH3:19]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 107545835-(Toluene-4-sulfonyl)-thiazolidine-2,4-dione

HCID 14357405Diethyldiazodicarboxylate

HCID 162169172,4-Diethoxybenzyl alcohol

Product 1

HCID 226780993-(2,4-Diethoxybenzyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione

Procedure

5-(Toluene-4-sulfonyl)thiazolidine-2,4-dione [U.S. Pat. No. 5,605,918; February 1997; Wrobel, et al.] was reacted with 2,4-diethoxybenzyl alcohol in the presence of triphenylphosphine and diethyl diazodicarboxylate to give the title compound as colorless crystals, mp 121-123° C.

Sources & evidence

ORD record: ord-14df3e62c643482fa0b8dc29630da06c
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605628B1

Reaction notes

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