Methyl 2-aminothiazole-5-carboxylate

Uses

Methyl 2-Aminothiazole-5-carboxylate (cas# 6633-61-0) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of methyl 2-aminothiazole-5-carboxylate from methyl 2-chloro-3-oxopropionate and compound (CAS:17356-08-0): a mixture of 2.4 g of methyl 2-chloro-3-oxopropionate, 20 mL of water, and 1.75 g of thiourea was refluxed for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature, decolorized by adding 0.25 g of activated carbon (Norit) and filtered. The filtrate was adjusted to neutral pH by slowly adding 2.5 N sodium hydroxide solution to the filtrate.The precipitate was collected by filtration to give 1.23 g (44% yield) of methyl 2-aminothiazole-5-carboxylate.

References

[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 3, p. 349 - 352
[2] Patent: WO2003/97616, 2003, A1. Location in patent: Page/Page column 26
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 5799
[4] Ann. Rep. Res. Inst. Tuberc. Kanazawa Univ., 1953, vol. 11, # 2, p. 39,41
[5] Chem.Abstr., 1955, p. 8250