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24th January 2013 @ 00:16
Mnr: MNR81-90

Synthesis of (Z)-2-((4-hydroxyphenyl)imino)thiazolidin-4-one (MNR88-1) from commercially available N-(4-Hydroxyphenyl)thiourea

Prep from ZYH14-1 As for MNR70-1

 

 

Hazard Assessment

HIRAC MNR70.pdf

Procedure

Reaction on at 1100, 24/01/13

To a mixture of  N-(4-Hydroxyphenyl)thiourea (1.03 g, 6.12 mmol) and sodium acetate trihydrate (0.83 g, 6.12 mmol) in ethanol (6 mL) was added ethyl bromoacetate (0.68 ml, 6.12 mmol) dropwise and the mixture was heated to 60 °C for 20 hours.  The reaction was allowed to cool to room temperature then ice was added at which point a a light brown precipitate formed.  This was filtered and washed with water and dried under vacuum.

 

It was unclear from the NMR is the solid was pure product so it was dissolved in MeOH and heated then allowed to cool to room temperature before being filtered to give a light brown solid (0.758 g, 3.6 mmol, 59%)

TLC

NMR

mnr88-1_filter_1H.pdf
mnr88-1_filter.zip
mnr88-1_MeOHwash_1H.pdf
MNR88-1_MeOHwash.zip


1H NMR matches that of compound 3 from http://dx.doi.org/10.1016/j.bmc.2010.05.073

Conclusion


The washing with MeOH stp was not needed as the NMR matches that of the literature.

Strings

Starting materials

InChI=1S/C7H8N2OS/c8-7(11)9-5-1-3-6(10)4-2-5/h1-4,10H,(H3,8,9,11)

InChI=1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3

Product 

InChI=1S/C9H8N2O2S/c12-7-3-1-6(2-4-7)10-9-11-8(13)5-14-9/h1-4,12H,5H2,(H,10,11,13)

Attached Files
MNR88-1_table.PNG
MNR88_scheme.png
mnr88-1_MeOHwash_1H.pdf
mnr88-1_filter_1H.pdf
MNR88-1_MeOHwash.zip
mnr88-1_filter.zip