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11th October 2011 @ 00:53
Product obtained in 84% yield.

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Preparation of 2-phenyliminothiazolidin-4-one from N-phenylthiourea and ethyl bromoacetate.1

Reaction Scheme

Reaction start time: 10.30 11/10/11
N-phenylthiourea (8.0 g, 52.6 mmol, 1.02 equiv.) and sodium acetate trihydrate (7.2 g, 52.6 mmol, 1.02 equiv.) were stirred in EtOH (25 mL). Ethyl bromoacetate (5.7 mL, 51.5 mmol, 1 equiv.) was added and the reaction heated to reflux. After 4 hours, reaction was poured over ice (130 mL). After the ice had melted the solid was filtered and recrystallised from hot EtOH (approx 150 mL) to obtain fine tan crystals (8.52 g, 84%). Consistent with SM thiourea by TLC. very old bottle of phenylthiourea used. 1H NMR in DMSO consistent with literature.2,3 CDCl3 NMR not consistent with literature.1

NMR:
1H NMR in DMSO
1H NMR in CDCl3


Risk and Hazard Assessement:
Risk Assessment


References:
  1. doi: 10.1016/j.bmc.2008.10.032

  2. doi: 10.1021/jo702369f
  3. doi: 10.1021/jm060545p
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Reaction Scheme
Risk Assessment
1H NMR in DMSO
1H NMR in CDCl3