2-aminothiazole

2-Aminothiazole is a heterocyclic compound that consists of a thiazole ring substituted with an amino group. It is a colorless solid that is soluble in polar solvents. 2-Aminothiazole is a key building block in pharmaceuticals and is used in the synthesis of various drugs.

Structure and Properties

2-Aminothiazole features a five-membered C3NS ring. The amino group is located at the 2-position of the thiazole ring. The molecule is planar, a feature it shares with other thiazoles. The compound is a weak base, with a pKa of 3.8 for the conjugate acid.

Synthesis

2-Aminothiazole can be synthesized by the reaction of thiocyanate with ammonia in the presence of a base. This reaction is known as the Cook-Heilbron thiazole synthesis, named after the chemists who first reported it.

Applications

2-Aminothiazole is a key building block in the synthesis of various pharmaceuticals. It is used in the production of cefuroxime, a second-generation cephalosporin antibiotic. It is also used in the synthesis of riluzole, a drug used to treat amyotrophic lateral sclerosis (ALS).

Safety

Like many amines, 2-aminothiazole is a skin and eye irritant. It is also harmful if swallowed or inhaled. Appropriate safety measures should be taken when handling this compound.

See Also

• Thiazole
• Amino group
• Heterocyclic compound
• Cefuroxime
• Riluzole