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9th January 2013 @ 06:58
Mnr: MNR61-70
Scaled up synthesis of (Z)-2-((3-hydroxyphenyl)imino)thiazolidin-4-one (MNR70-2) from MNR69-1.

Prep from ZYH14-1
As for MNR70-1

MNR70_scheme.png
MNR70-2_table.PNG

Hazard Assessment
HIRAC MNR70.pdf


Procedure

Reaction on at 1800, 09/01/13

To a mixture of MNR69-1 (3.10 g, 18.4 mmol) and sodium acetate trihydrate (2.51 g, 18.43 mmol) in ethanol (20 mL) was added ethyl bromoacetate (2.0 ml, 18.4 mmol) dropwise and the mixture was heated to 60 °C for 16 hours.

The reaction was allowed to cool to room temperature then ice was added. Nothing significant precipitated out, only what looked like an oily side product. The Reaction mixture was then extracted with EtOAC (25 ml x 2). The organic fractions were combined, dried over MgSO4, filtered and concentrated to give a dark orange oil ( g).

TLC

NMR

Conclusion

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

Product
InChI=1S/C9H8N2O2S/c12-7-3-1-2-6(4-7)10-9-11-8(13)5-14-9/h1-4,12H,5H2,(H,10,11,13)
Attached Files
MNR70-2_table.PNG