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13th October 2011 @ 23:55
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Condensation of 2-phenyliminothiazolidin-4-one (PMY 13-1) and PMY 2-4 to obtain the iminothiazolidinone substituted 4-fluorophenylpyrrole analogue of "near neighbours".

Reaction Scheme

Reaction start time: 10.50 14/10/11
PMY 2-4 (200 mg, 0.92 mmol, 1 equiv.), PMY 13-1 (177 mg, 0.92 mmol, 1 equiv.) and sodium acetate (251 mg, 1.84 mmol, 2 equiv.) were heated at 100 °C in AcOH (15 mL) and Acetic anhydride (3 mL). After 2.5 hours, reaction was poured onto ice and diluted with EtOAc (25 mL). Layers separated and the aqueous extracted with EtOAc (2 × 20 mL). The Organic layers were washed with saturated NaHCO3 (3 × 10 mL), water (3 × 15 mL) and brine then dried (MgSO4) and concentrated under reduced pressure to a green gum. Purified by chromatography (0-50% EtOAc/hexane) to obtain 2 products, (59 mg) and product fractions, yellow solid (72 mg), more polar than either SM. Later fractions consistent with expected product by 1H NMR but not clean. Submitted for MS.

m/z (ESI+) 392 [M+H]+, 25%; 434 [M+Ac+H]+, 75%; 456 [M+Ac+Na], 95%; 889 [2(M+Ac)]+, 100%.

Mass spec indicates Acetylated product formed, not intended product!
NMR consistent with mass spec. See: Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-1)

Reaction Scheme

NMR:
1H early fraction
1H NMR later fraction


Risk and Hazard Assessment:
Risk Assessment


See also:
Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-1)
Preparation of 2-phenyliminothiazolidin-4-one (PMY 13-1)
Linked Posts
Attached Files
Reaction Scheme
1H early fraction
1H NMR later fraction
New product scheme
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