2-(Methylthio)-2-thiazoline

Uses

thiazolidin e thione pharmaceutical intermediate

Uses

2-(Methylthio)-2-thiazoline has been used in the preparation of:

• novel tri- and tetracyclic hetero systems, via reaction with heteroaromatic 2-aminoesters
• 2-(2-chlorobenzylamino)-2-thiazoline

Synthesis

General procedure for the synthesis of 2-methylthio-2-thiazoline from thiazolidine-2-thione and iodomethane: Thiazolidine-2-thione (2 g, 0.0168 mol) was dissolved in acetonitrile (20 ml) and iodomethane (1.04 ml, 0.0168 mol) was added. The reaction mixture was heated to reflux for 3 hours and subsequently cooled to room temperature. The reaction mixture was filtered and the white solid obtained was collected. The solid was poured into saturated potassium carbonate solution (20 ml) to form an oil. The oily substance was extracted with dichloromethane and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a colorless liquid product (1.4 g, 63% yield).

References

[1] Synthetic Communications, 2006, vol. 36, # 22, p. 3339 - 3343
[2] Patent: CN105481846, 2016, A. Location in patent: Paragraph 0006; 0007
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 3335,3338
[4] Journal of Organic Chemistry, 1961, vol. 26, p. 85 - 88
[5] Helvetica Chimica Acta, 1978, vol. 61, p. 3143 - 3148