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

Synthesis of near neighbour analog MNR95-1 from pyrrole AEW49-1 and thiazolidinone MNR88-1.

 InChI=1S/C22H19N3O2S/c1-14-12-16(15(2)25(14)18-6-4-3-5-7-18)13-20-21(27)24-22(28-20)23-17-8-10-19(26)11-9-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-13-

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone MNR88-1 (0.08 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 an orange solid (0.125 g, 0.32 mmol, 80%)

NMR

 

mnr95-1_1H.pdf
mnr95-1.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/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)

Product

InChI=1S/C22H19N3O2S/c1-14-12-16(15(2)25(14)18-6-4-3-5-7-18)13-20-21(27)24-22(28-20)23-17-8-10-19(26)11-9-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-13-

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31st January 2013 @ 07:27
Mnr: MNR91-100

Synthesis of near neighbour analog MNR94-1 from pyrrole AEW49-1 and thiazolidinone MNR70-2.

 

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone  MNR70-2 (0.08 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 dark yellow solid (0.124 g, 0.32 mmol, 79%)

NMR

 

mnr94-1_1H.pdf
mnr94-1.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/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)

Product

InChI=1S/C22H19N3O2S/c1-14-11-16(15(2)25(14)18-8-4-3-5-9-18)12-20-21(27)24-22(28-20)23-17-7-6-10-19(26)13-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-12-

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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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