All Notebooks | Help | Support | About
16th August 2013 @ 01:35

Synthesised using direct method but also see Hydrolysis of acyl-iminothiazolidinone PMY 14-1 (PMY 16-1) for reference.

(PMY 13-1) (135 mg, 0.70 mmol, 1.02 equiv.) was dissolved in ethanol (10 mL) and combined with piperidine (0.11 mL, 1.11 mmol, 1.61 equiv.). AEW 2-3 (150 mg, 0.627 mmol, 1.00 equiv.) was dissolved in ethanol (5 mL) and added to the mixture, and the resulting clear brown solution was heated to 60 °C for 2.5 h 


Data

AEW 80-1 check.zip
AEW 80-1.pdf

Hazard and Risk Assessment:

See Synthesis of (2Z,5Z)-5-((2,5-dimethyl-1-(p-tolyl)-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one (AEW 76-1, OSM-S-37)

Linked Entries
This entry is linked by:
Attached Files
16th August 2013 @ 01:12

For original synthesis see here. Resynthesised for characterisation and possible submission to new assay.

Going to start at 4.30pm

AEW 76-1 (50 mg, 0.13 mmol, 1 equiv.) was dissolved partially in toluene (~5 mL) and stirred under a nitrogen atmosphere. Pyridine (~20 μL, 0.25 mmol, 1.9 equiv.) was added, followed by acetic anhydride (~40 μL, 0.4 mmol, 3 equiv.). The mixture was heated to 80 °C and left stirring overnight under nitrogen.

Hazard and Risk Assesment:

See Acetylation of para-trifluoromethyl near neighbour analogue (ZYH 12-1)

Linked Posts
This post is linked by:
Attached Files
13th August 2013 @ 08:02

Resynthesis of OSM-S-37, See ZYH 5-1 for original expt.

2-phenyliminothiazolidin-4-one (PMY 13-1) (123 mg, 0.640 mmol, 1.02 equiv.) was dissolved in ethanol (10 mL) and combined with piperidine (0.100 mL, 1.01 mmol, 1.61 equiv.). 2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrole-3-carboxaldehyde (LMW 5-1) (145 mg, 0.627 mmol, 1.00 equiv.) was dissolved in ethanol (5 mL) and added to the mixture, and the resulting clear brown solution was heated to 60 °C for 2.5 h then removed from the heat and stirred at room temperature o/n. Reaction mixture cooled and stirred in an ice bath and then filtered to yield a yellow solid. First filtration, solid passed through and blocked sinter. Re-filtered using fine grade filter paper to give a bright yellow solid that was dried at the high vac (x mg). Sinter funnel washed with EtOAc and the illuminous yellow mother liquors were concentrated to yield

Hazard and Risk Assessment:

See Synthesis of p-methyl arylpyrrole based near neighbour (ZYH 5-1)

Linked Entries
Attached Files
16th January 2013 @ 22:46

dark brown oil: 754 mg, 3.77 mmol, 106% yield - need to check

DMF (1.5 mL) was stirred under a nitrogen atmosphere in an ice-bath. Phosphoryl chloride (0.397 mL, 4.24 mmol, 1.2 equiv.) was added and the reaction stirred for 25 minutes. A solution of pyrrole AEW 37-1 (609 mg, 3.54 mmol, 1 equiv.) in DMF (1.5 mL) was added dropwise over 5 minutes. The reaction was removed from the ice-bath and allowed to warm to room temperature.

TLC:

NMR:

Hazard and Risk Assessment:

Linked Posts
This post is linked by:
Attached Files
16th January 2013 @ 22:40

one batch black solid, one batch mustard solid: combined: 2.3 g, 11.5 mmol, 64% yield

DMF (5 mL) was stirred under a nitrogen atmosphere in an ice-bath. Phosphoryl chloride (2 mL, 21.7 mmol, 1.2 equiv.) was added and the reaction stirred for 25 minutes. A solution of pyrrole AEW 44-1 (3.1 g, 18.1 mmol, 1 equiv.) in DMF (5 mL) was added dropwise over 5 minutes. The reaction was removed from the ice-bath and allowed to warm to room temperature.

TLC:

NMR:

Hazard and Risk Assessment:

Linked Posts
This post is linked by:
Attached Files