Trichloroethanol → HCID 178458018, compound

Participants

Reaction Steps

To a stirring solution of 3-tert-butyl-1-isopropyl-1H-pyrazole-5-carboxylic acid (7.92 g, 38 mmol) and triethylamine (5.7 g, 56 mmol) in 1,4-dioxane (80 mL) was added diphenylphosphoryl azide (12 g, 44 mmol). The resultant reaction mixture was stirred 30 min at RT. 2,2,2-Trichloroethanol (78 g, 527 mmol) was added and the reaction was heated to 100° C. After 4 h, the completed reaction was diluted with brine and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Purification of the residue by chromatography provided 2,2,2-trichloroethyl 3-tert-butyl-isopropyl-1H-pyrazol-5-ylcarbamate (4.0 g, 31% yield). 1H-NMR (400 MHz, DMSO-d6): 9.85 (s, 1 H), 5.94 (s, 1 H), 4.90 (s, 2 H), 4.37 (m, 1 H), 1.27 (d, J=7.2 Hz, 6 H), 1.18 (s, 9 H). MS (ESI) m/z: 356.1 (M+H+).

Provenance & Evidence