April 18, 2024, 11:02:20 PM
Forum Rules: Read This Before Posting


Topic: Mechanism for replacement of SCH3 by OH using 2-mercaptoethanol?  (Read 685 times)

0 Members and 1 Guest are viewing this topic.

Offline GinaTageldin

  • Regular Member
  • ***
  • Posts: 76
  • Mole Snacks: +1/-2
  • Gender: Female
i have 4-aryl-1-methyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile derivative
and i reacted it with 2-mercaptoethanol in dichloromethane and DIPEA at room temperature for 14 h, the resulted product revealed removal of the methylsulfanyl moiety and introduction of a OH group?
Also i reacted the same compound with oxone and yielded the same product? Any explanation for the mechanism using 2-mercaptoethanol

Offline pgk

  • Chemist
  • Full Member
  • *
  • Posts: 892
  • Mole Snacks: +97/-24
Re: Mechanism for replacement of SCH3 by OH using 2-mercaptoethanol?
« Reply #1 on: March 18, 2020, 01:52:31 PM »
Think about a DIPEA catalyzed, thiirane formation that liberates a hydroxyl anion, which attacks to the 2 position and liberates the methylsulfanyl group. The transition intermediate is stabilized by conjugation with the nitrile group, through the unsaturated ring.

Sponsored Links