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21st February 2012 @ 00:21
Desired product synthesised in 72% yield.

01/06/12: X-ray structures confirms acyl group on the N-phenyl rather than the thiazolidinone nitrogen.

x-ray image

x-ray data


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Acetylation of PMY 14-4 to obtain the acetylated 4-fluoro compound consistent with PMY 14-1. Method from ZYH 12-2.

PMY35-1.png

Reaction Start Time: 13.40 EST 21/02/12
PMY 14-4 (286 mg, 0.73 mmol, 1 equiv.) was stirred in PhMe (10 mL) with pyridine (0.12 mL, 1.46 mmol, 2 equiv.). Acetic anhydride (0.3 mL, 2.92 mmol, 4 equiv.) was added and the yellow slurry heated to 100 °C. After 3 hours 20 minutes, TLC shows formation of a new product, SM still remains. After 21 hours, reaction is complete by TLC. Yellow solution and yellow precipitate. Hexane (10 mL) was added, briefly stirred and the reaction was filtered to obtain a yellow powder (227 mg, 72%) consistent with PMY 4-1 and 14-2 by 1H NMR, quite clean but contains a broad peak at 1.6 ppm and a sharp singlet at ~2.65 ppm. The filtrate was concentrated under reduced pressure to yield a small amount of yellow/orange powder, not kept.

28 Feb: TLC of solid stored at room temperature (in light) shows product to be a single spot.

TLC (10% MeOH/DCM) visualised with UV and vanillin:
TLC vanillin stained
TLC under visible light

3 hours 20 minutes: left plate is unstained and photographed under visible light (yellow compounds). Right plate is stained with vanillin.
TLC 28 Feb


NMR:
1H NMR


Risk and Hazard Assessment:
See: Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-2) and also Acetylation of para-trifluoromethyl near neighbour analogue (ZYH 12-1)

See also:
Synthesis of 4-Fluoro substituted near neighbour (PMY 14-4)
Acetylation of para-trifluoromethyl near neighbour analogue (ZYH 12-2)
Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-1)
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Attached Files
Scheme
TLC under visible light
TLC vanillin stained
TLC 28 Feb
1H NMR
x-ray image
x-ray data