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6th March 2012 @ 08:38

Condensation of 1-(3-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (SBBH-1-5) with 3-phenyl-2-(phenylimino)thiazolidin-4-one (SBBH-1-7)

Reaction time: 03-02-12 (11.50 IST)

Experimental Procedure: To a stirred solution of 3-phenyl-2-(phenylimino)thiazolidin-4-one (SBBH-1-7) (0.123g, 1 equiv, 0.46 mmol) in ethanol (10 mL), piperidine (67µL, 1.5 equiv, 0.69 mmol) was added. The mixture solution was transferred to oil bath at 60 oC. SBBH-1-7 was not dissolved properly in ethanol. After 40 minutes of heating SBBH-1-7 almost dissolved then ethanolic solution of 1-(3-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (SBBH-1-5) was added drop wise. Instantly colourless solution turned into deep yellow coloured solution. First TLC was checked at 1.5 h. of reaction starting, a new less polar spot was present just above the starting materials. The product spots were visualized in UV and developed under I2 vapour. Next TLC was checked after 2.5 h. which indicated incomplete reaction. After 4.5 h TLC was checked again but it could not be confirmed whether both reactants SBBH-1-5 or SBBH—1-7 were completely consumed as the respective spots were not visible in I2 vapour but only in UV light. Next morning (9.0 AM) TLC was checked again but no change was observed. So the reaction was removed from heating and cooled to room temperature. Thereafter ethanol was evaporated under reduced pressure to obtain a yellow oil semi solid mass. The residue was extracted with EtOAc (40 mL) and water (20 mL). The organic layer was collected washed with brine (10 mL), dried over Na2SO4and evaporated under reduced pressure. The residue was purified via column chromatography over silica gel (230-400 mesh) using 3-4: 97-96 % ethyl acetate and hexane as eluent.The desired compound was obtained as yellow solid (0.072 g, 33.2% yield).

TLC after 1.5 hour (40% ethyl acetate in hexane) visualised using UV and I2:

SBBH-1-9 1.5 hr.jpg

TLC after 2.5 hour (40% ethyl acetate in hexane) visualised using UV and I2:

SBBH-1-9 2.5 hr.jpg

TLC after 4.5 hour (40% ethyl acetate in hexane) visualised using UV and I2:

SBBH-1-9 4.5 HR.jpg

1H NMR:

SBBH-1-9 (1H).pdf
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Attached Files
diphenylthiazolidine finalcomp.png
SBBH-1-9 1.5 hr.jpg
SBBH-1-9 2.5 hr.jpg
SBBH-1-9 4.5 HR.jpg
SBBH-1-9 (1H).pdf
Mass spectra
IR spectrum
1H RAW data
SBBH-1-9 (13C)
13C RAW data
HRMS
SBBH-1-9 (19F)
SBBH-1-9 (19F) RAW DATA