Trichloroacetonitrile → 2-(trichloromethyl)-1H-imidazole

To a stirred solution of trichloroacetonitrile (28.8 g, 200 mmol, 1 eq) in anhydrous THF (70 mL) at −60° C. under an argon atmosphere, 2,2-dimethoxyethanamine (C-1) (21.8 mL, 200 mmol, 1.0 eq) is added dropwise over 5 min. The resulting mixture is allowed to warm to RT and stirred at RT for 4 h. The mixture is concentrated in vacuo and the residue is added in portions to a stirred solution of trifluoroacetic acid (100 mL) at −30° C. under argon. The resulting mixture is then stirred from −30° C. to RT overnight. The reaction mixture is concentrated in vacuo to afford the product, 2-(trichloromethyl)-1H-imidazole (C-2). The product is used in the next step without further purification.

1. concentrationThe mixture is concentrated in vacuo
2. additionthe residue is added in portions to a stirred solution of trifluoroacetic acid (100 mL) at −30° C. under argon
3. stirringThe resulting mixture is then stirred from −30° C. to RT overnight
4. concentrationThe reaction mixture is concentrated in vacuo

ORD record

ord-19eedc643924499f85843ebf2d754d99

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181221B2