(5Z)-5-(3-ethoxy-4-hydroxybenzylidene)-3-(3-fluorophenyl)-2-thioxo-1,3-thiazolidin-4-one synthesis
- Product Name:(5Z)-5-(3-ethoxy-4-hydroxybenzylidene)-3-(3-fluorophenyl)-2-thioxo-1,3-thiazolidin-4-one
- CAS Number:1198159-38-4
- Molecular formula:C18H14FNO3S2
- Molecular Weight:375.44
Yield:1198159-38-4 22%
Reaction Conditions:
with ammonium acetate;acetic acid at 130; for 48 h;
Steps:
3.2
To a solution of 3 -fluorophenyl rhodanine (100 mg, 0.44 mmol) and 3-ethoxy-4-hydroxy benzaldehyde (73 mg, 0.44 mmol, 1.0 eq) in glacial acetic acid (10 mL) was added ammonium acetate (102 mg, 1.3 mmol, 3.0 eq,). The resulting clear solution was refluxed at 130 0C for 2 days, then cooled to room temperature and poured into water (30 mL). The mixture was stirred for 15 min, and then the solids were filtered, washed with water (2 x 20 mL) and dried to yield a yellow solid. The solid was recrystallized from CH3CN to yield 37 mg (22%) of product as a yellow granular solid.1H-NMR (DMSO-J6): δ 10.20 (s, IH), 7.77 (s, IH), 7.62-7.58 (m, IH), 7.43-7.37 (m, 2H), 7.20 (dd, IH), 7.24 (s, IH), 7.18 (dd, IH), 6.99 (d, IH), 4.1 1 (q, 2H), 1.38 (t, 3H).
References:
WO2009/142720,2009,A1 Location in patent:Page/Page column 33
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