Diisopropylethylamine → HCID 136119101, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (9.03 g, 130 mmol) was added to a solution of 1,3-thiazole-2-carbaldehyde (14.71 g, 130 mmol) and pyridine (10.5 mL, 130 mmol) in DCM (100 mL). The reaction mixture was stirred overnight at room temperature and then washed twice with water. The organic layer was dried over MgSO4 and then evaporated under reduced pressure to give 15.26 g of 1,3-thiazole-2-carbaldehyde oxime (yield 92%). 1,3-thiazole-2-carbaldehyde oxime (15.23 g, 119 mmol, 1 equiv) was dissolved in 80 mL of dioxane and then TEA (41.4 mL, 2.5 equiv) was added. The reaction mixture was cooled to 0° C. and then trifluoroacetic anhydride (18.3 mL, 1.1 equiv) was added dropwise to the reaction. The solution was stirred overnight at room temperature and then evaporated. The residue was dissolved in DCM and then washed twice with water. The organic layer was dried over MgSO4 and then evaporated under reduced pressure to give 1,3-thiazole-2-carbonitrile. This compound was used in the next step without further purification. 1,3-thiazole-2-carbonitrile (13.11 g, 119 mmol, 1 equiv), hydroxylamine hydrochloride (12.4 g, 1.5 equiv) and DIEA (33 mL, 1.6 equiv) were mixed in absolute EtOH (150 mL). The reaction mixture was refluxed 4 h and then the solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt, washed twice with water and once with brine. The organic layer was dried over MgSO4 and then evaporated under reduced pressure to give 15.86 g of 1,3-thiazole-2-amidoxime (yield 93% over two steps).

Provenance & Evidence