5-(4-(2-(3-METHOXYPHENYL)-2-OXOETHOXY)BENZYL)THIAZOLIDINE-2,4-DIONE synthesis
- Product Name:5-(4-(2-(3-METHOXYPHENYL)-2-OXOETHOXY)BENZYL)THIAZOLIDINE-2,4-DIONE
- CAS Number:1133819-87-0
- Molecular formula:C19H17NO5S
- Molecular Weight:371.41
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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Yield: 77%
Reaction Conditions:
with 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate for 5 h;Reflux;
Steps:
16 6.16. 5-[[4-[2-(4-Methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-2,4-thiazolidinedione 7
To a solution of 5-[[4-[2-(4-methoxyphenyl)-2-hydroxyethoxy]phenyl]methyl]-2,4-thiazolidinedione 24b (2.82 g, 7.55 mmol) in EtOAc (25 mL) was added 2-iodoxybenoic acid (1.23 g, 4.4 mmol).
The mixture was heated to reflux for 5 h at which point it was judged (HPLC) to be ca.
50% complete and an additional 1.50 g (5.35 mmol) of IBX was added.
After an additional 5 h at reflux, HPLC analysis indicated that the reaction was complete and the mixture was cooled to room temperature and filtered through a small pad of silica and the pad was rinsed with EtOAc.
The solvent was removed in vacuo and the residue was purified by chromatography on a column of silica gel using the flash technique (40 mm OD, 100 g, 230-400 mesh), eluting with 0-15% EtOAc-CH2Cl2.
Fractions containing 7 were pooled to give 7 (2.15 g, 77%) as a pale tan solid. 1H NMR (400 MHz, DMSO-d6): δ = 12.03 (s, 1), 7.62 (d, J = 7.7 Hz, 1), 7.45-7.51 (2), 7.26 (m, 1), 7.16 (d, J = 8.6 Hz, 2), 6.91 (d, J = 8.6 Hz, 2), 5.55 (s, 2), 4.88 (m, 1), 3.84 (s, 3), 3.31 (dd, J = 14.2, 4.2 Hz, 1), 3.05 (dd, J = 14.2, 9.2 Hz, 1); MS (ESI+) m/z 394.3 (M+Na); MS (ESI-) m/z 370.3 (M-H); Anal. Calcd. For C19H17NO5S C, 61.44; H, 4.61; N, 3.77. Found: C, 61.29; H, 4.52; N, 3.57.
References:
Tanis, Steven P.;Colca, Jerry R.;Parker, Timothy T.;Artman, Gerald D.;Larsen, Scott D.;McDonald, William G.;Gadwood, Robert C.;Kletzien, Rolf F.;Zeller, James B.;Lee, Pil H.;Adams, Wade J. [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 22,p. 5870 - 5884]
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1133819-87-0
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5000-65-7
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74772-78-4
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![2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-](/CAS/GIF/103788-60-9.gif)
103788-60-9
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1133819-87-0
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