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14th November 2013 @ 18:07

reaction scheme

1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole: p-Anisidine (.614g, 5.0mmol) was combined with 2,5-hexanedione and heated overnight (130°C). Product was dissolved in 2 tube volumes of ether and 2 tube volumes of 10% citric acid. After separation of layers, the organic layer was washed with H2O (10 mL) and NaCL in solution (10 mL). The solution was dried with MgSO4. Filtrate was concentrated under reduced pressure. The resulting solid was dissolved in a minimal (<5 mL) amount of hot ethanol. The solution was allowed to cool and water was added dropwise until the solution became cloudy (4 drops). Solution transferred into ice-cold beaker for further crystallization. Vacuum filtration was used to filter the solution and separate out the product (0.258 g). Melting point of substance was 59.7-59.8 oC. FTIR: 3012, 3004, 2958 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.89-7.86 (m, 2H), 7.77-7.75 (m, 2H), 6.0 (s, 2H), 4.1 (s, 3H), 2.1 (s, 6H).

1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde: An ice bath was created in which POCl3 (0.144mL, 1.54mmol) and DMF (1.0mL) were added and stirred (25 min). DMF (1.0mL) was added to the above pyrrole (258mg, 1.28mmol). The two solutions were combined dropwise (5 min). Allowed reaction to warm to room temp until reaction was complete (monitored via TLC). Poured reacted material over ice. Added NaOH (approx. 6mL) dropwise (monitored pH with pH paper). The reaction was filtered under vacuum. The solid was allowed to dry overnight and then massed (172mg, 66.6%). Melting Point: 140.1°C to 141.7°C. IR: 3100, 2933, 1650.89, 1513.56 cm-1; 1H-NMR (400MHz, CDCl3) δ 9.867 (s, 1H), 7.26 (s, 1H), 7.10 (d, J= 6.8Hz, 2H), 7.01 (d, J=6.8Hz, 2H), 6.367 (s, 1H), 3.879 (s, 3H), 2.269 (s, 3H), 1.979 (s, 3 H).

Thiazolidinone Pyrrole: (Z)-2-((3-phenyl)imino)thiazolidin-4-one (0.1297 g, 0.675 mmol) was dissolved in ethanol (0.6 mL). Piperidine (0.1 mL, 1.0125 mmol) was added to this solution. The aldehyde synthesized above (0.1548g, 0.675 mmol) was combined with this solution. The solution heated at 60 °C overnight until completion (monitored by TLC). The resulting solid was filtered under vacuum. The resulting brown crystals were the final product (0.1560 g, 59.6%). The melting point was 279.0-279.5 °C. FTIR: 3401, 3093, 3054, 2943, 1628, 1590 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.73 (s, 1H), 7.41, (t, 2H) 7.22 (m, 3H) 7.07 (d, 2H), 6.98 (d, 2H), 6.11 (s, 1H), 3.86 (s, 3H), 2.13 (s, 3H), 1.97 (s, 3H). 

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Attached Files
pOCH3-aldehyde-1H.pdf
pOCH3-final-1H.pdf
PNP-p-OCH3.SPA
pOCH3-aldehyde-1H.fid
pOCH3-final-1H.fid
PNP-pOMe-scheme.png
PNP-pOCH3-IR.pdf