(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → HCID 10270502, compound

Participants

Reaction Steps

A suspension of N-[(2S)-oxiran-2-ylmethyl]-phthalimide (18.4 g, 90.6 mmol) and 2-mercaptobenzothiazole (15.8 g, 94.5 mmol) in EtOH (530 mL) was heated to reflux for 14.5 h. The reaction was then cooled and concentrated under reduced pressure. The crude mixture was crystallized from ethanol and filtered to provide N-[(2S)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide (25.5 g, 76%) as a solid. Data for N-[(2S)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide: 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.75 (m, 4H), 7.45-7.26 (m, 2H), 5.15 (m, 1H), 4.42 (m, 1H), 4.08-3.88 (m,2H, 3.61 (m, 1H), 3.42 (m, 1H).

Provenance & Evidence