Water → 5-(3-acetylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

Participants

Reaction Steps

Triethylamine (14.2 mmol) and DMAP (4.00 mmol) are added to a solution of 5-(3-Amino-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (4.00 mmol) in acetic acid anhydride (25 mL). After 30 min EtOAc and water are added, the layers are separated and the aqueous layer is extracted once with EtOAc. The combined organic layers are washed twice with sat aqueous ammonium chloride solution, once with sat aqueous NaHCO3 solution and once with water and the solvents are removed in vacuo. The residue is diluted with EtOAc and extracted three times with sat aqueous NaHCO3 solution. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude solid which is diluted with ether. The obtained suspension is filtered and the residue is washed with ether to give the desired acetamide. LC-MS: tR=0.81 min; [M+H]+=291.3.

Provenance & Evidence