Dimethylformamide → HCID 71253084, compound

Participants

Reaction Steps

N,N-dimethylformamide (0.27 mL, 3.47 mmol) was added to a solution of tetrahydropyranyl-4-acetic acid (5.0 g, 34.7 mmol) and thionyl chloride (2.53 mL, 34.7 mmol) in DCM (200 mL) at 0° C. After stirring 1 h at RT the solution was cooled to 0° C. N-Ethyl-N-isopropylpropan-2-amine (15.14 mL, 87 mmol) was added, followed by 4-bromoaniline (5.97 g, 34.7 mmol) in 20 mL DCM were added slowly and the solution was stirred at 0° C. After 1 h the reaction was diluted with saturated ammonium chloride and the organics were removed. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material N-(4-bromophenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide as a tan solid.

Provenance & Evidence