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31st January 2013 @ 07:20
Mnr: MNR91-100

Synthesis of near neighbour analog MNR93-1 from pyrrole AEW49-1 and thiazolidinone PMY13-1.  Repeat synthesis of OSM-S-35

 

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone PMY13-1 (0.077 g, 0.4 mmol) was dissolved in ethanol (6 mL) and piperdine (0.06 mL, 0.6 mmol) was added.  AEW49-1 (0.080 g, 0.4 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight.  The reaction was then allowed to cool to room temperature and the precipitate was filtered and washed with EtOH to give a mustard coloured solid (0.065 g, 0.174 mmol, 43%) - product lost on the vac-line

NMR

 

mnr93-1_1H.pdf
mnr93-1.zip

Conclusion

Proton NMR looks good and sample is ready to send for testing, further characterisation still needed.

Strings

Starting Materials

InChI=1S/C13H13NO/c1-10-8-12(9-15)11(2)14(10)13-6-4-3-5-7-13/h3-9H,1-2H3

InChI=1S/C9H8N2OS/c12-8-6-13-9(11-8)10-7-4-2-1-3-5-7/h1-5H,6H2,(H,10,11,12)

Product

InChI=1S/C22H19N3OS/c1-15-13-17(16(2)25(15)19-11-7-4-8-12-19)14-20-21(26)24-22(27-20)23-18-9-5-3-6-10-18/h3-14H,1-2H3,(H,23,24,26)/b20-14-

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30th January 2013 @ 07:20
Mnr: MNR91-100

Synthesis of near neighbour analog MNR91-1 from pyrrole AEW50-1 and thiazolidinone MNR88-1

 

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone MNR88-1 (0.072 g, 0.35 mmol) was dissolved in ethanol (5 mL) and piperdine (0.05 mL, 0.52 mmol) was added. AEW50-1 (0.070 g, 0.35 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight.  THe reaction was then allowed to cool to room temperature and the precipitate was filtered and washed with EtOH to give an orange/brown solid (0.055 g, 0.14 mmol, 40%)

NMR

 

mnr92-1_1H.pdf
mnr92-1.zip

Conclusion

 Proton NMR looks good and sample is ready to send for testing, further characterisation still needed.

Strings

Starting Materials

InChI=1S/C12H12N2O/c1-9-7-11(8-15)10(2)14(9)12-5-3-4-6-13-12/h3-8H,1-2H3

InChI=1S/C10H9NO2S/c12-8-3-1-7(2-4-8)5-10-11-9(13)6-14-10/h1-5,12H,6H2,(H,11,13)/b10-5-

 

Product

InChI=1S/C22H19N3O2S/c1-14-11-17(15(2)25(14)20-5-3-4-10-23-20)13-19-22(27)24-21(28-19)12-16-6-8-18(26)9-7-16/h3-13,26H,1-2H3,(H,24,27)/b19-13-,21-12-

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30th January 2013 @ 07:11
Mnr: MNR91-100

Synthesis of near neighbour analog MNR91-1 from pyrrole AEW50-1 and thiazolidinone MNR70-2

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone MNR70-2 (0.072 g, 0.35 mmol) was dissolved in ethanol (5 mL) and piperdine (0.05 mL, 0.52 mmol) was added. AEW50-1 (0.070 g, 0.35 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight.  The reaction was then allowed to cool to room temperature but no precipitate formed.  THe reaction mixture was concentrated then dissolved in DCM (5 mL) and washed with water (5 mL).  The water was then washed with DCM (5 mL x 2), the organic layers were combined, dried over magnesium sulphate, filtered and concentrated to give the crude as brown oil (0.104 g).

NMR

 NMR of the crude extraction:- 

mnr91-1_crude_1H.pdf
mnr91-1_extract.zip

 

Potential signs of the product but this needs cleaned up

Column

only resulted in a mess

mnr91-1_frac22-34_1H.pdf

Conclusion


No clean product recovered, reaction not taken any further.  This needs repeated.

 

Strings

Starting Materials

InChI=1S/C12H12N2O/c1-9-7-11(8-15)10(2)14(9)12-5-3-4-6-13-12/h3-8H,1-2H3

 InChI=1S/C10H9NO2S/c12-8-3-1-2-7(4-8)5-10-11-9(13)6-14-10/h1-5,12H,6H2,(H,11,13)/b10-5-

 

Product

InChI=1S/C22H19N3O2S/c1-14-10-17(15(2)25(14)20-8-3-4-9-23-20)13-19-22(27)24-21(28-19)12-16-6-5-7-18(26)11-16/h3-13,26H,1-2H3,(H,24,27)/b19-13-,21-12-

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30th January 2013 @ 06:22
Mnr: MNR81-90

Synthesis of near neighbour analog MNR90-1 from pyrrole AEW50-1 and thiazolidinone PMY13-1

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone PMY13-1 (0.067 g, 0.35 mmol) was dissolved in ethanol (5 mL) and piperdine (0.05 mL, 0.52 mmol) was added. AEW50-1 (0.070 g, 0.35 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight.  The reaction was then allowed to cool to room temperature but no precipitate formed.  THe reaction mixture was concentrated then dissolved in DCM (5 mL) and washed with water (5 mL).  The water was then washed with DCM (5 mL x 2), the organic layers were combined, dried over magnesium sulphate, filtered and concentrated to give the crude as brown oil (0.144 g).  Column, not very succesful and no clean product recovered, further purification not attempted.  The reaction should be repeated if this compound is required in the future

NMR

 

Conclusion

Purification not very succesful and no clean product recovered, further purification not attempted.  The reaction should be repeated if this compound is required in the future

Strings

Starting Materials

InChI=1S/C12H12N2O/c1-9-7-11(8-15)10(2)14(9)12-5-3-4-6-13-12/h3-8H,1-2H3

InChI=1S/C10H9NOS/c12-9-7-13-10(11-9)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,11,12)/b10-6-

 

Product

InChI=1S/C22H19N3OS/c1-15-12-18(16(2)25(15)20-10-6-7-11-23-20)14-19-22(26)24-21(27-19)13-17-8-4-3-5-9-17/h3-14H,1-2H3,(H,24,26)/b19-14-,21-13-

Attached Files
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