Triethylamine hydrochloride → 7-Bromo-2,4-dichloroimidazo[2,1-f][1,2,4]triazine

Temperature

110 °C

(I9F): Phosphoryl trichloride (200 mL, 2178 mmol) was added to a mixture of 7-bromoimidazo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione (20 g, 87 mmol) and triethylamine hydrochloride (24 g, 174 mmol) in 500 ml pressure tube. The reaction was heated to 110° C. for 24 hrs. The reaction mixture was cooled to room temperature and concentrated using high vacuum pump. The residue was suspended in toluene and azotroped with toluene (3×250 ml). The residue was taken in a cooled mixture of 1000 ml of ethyl acetate and 500 ml of saturated sodium bicarbonate solution. The organic layer was separated. Aqueous layer was extracted with ethyl acetate (3×300 ml). Combined organic layer was washed with aqueous sodium bicarbonate solution (2×150 ml) and 100 ml of brine solution. The organic layer was dried over sodium sulphate and concentrated to give 51 g of 7-bromo-2,4-dichloroimidazo[2,1-f][1,2,4]triazine.

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated
3. additionThe residue was taken in a cooled mixture of 1000 ml of ethyl acetate and 500 ml of saturated sodium bicarbonate solution
4. customThe organic layer was separated
5. extractionAqueous layer was extracted with ethyl acetate (3×300 ml)
6. washCombined organic layer was washed with aqueous sodium bicarbonate solution (2×150 ml) and 100 ml of brine solution
7. dry with materialThe organic layer was dried over sodium sulphate
8. concentrationconcentrated

ORD record

ord-4921acb9abba4b989d42416d7dbb224c

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273057B2