Phosphorus oxychloride → HCID 13479940, compound

A solution of 500 mg (2.7 mmol) of 3-methylsulfanyl-5-oxo-4,5-dihydro-[1,2,4]triazine-6-carboxylic acid amide (J. J. Huang, J. Org. Chem. 1985, 50, 2293-2298; H. Wang et al., Hua Hsueh Hsueh Pao 1964, 30(2), 183-192; CA Vol. 61, 8311b) in 38 ml (408 mmol) of phosphorus oxychloride was heated to reflux during 1.5 h. After cooling of the dark brown reaction mixture, the excess of phosphorus oxychloride was evaporated under reduced pressure. To destroy residues of phosphorus oxychloride and to neutralize the reaction mixture, the resulting red-brown oily residue was dissolved in 15 ml of toluene and the solution added to an ice-cold saturated aqueous solution of sodium hydrogencarbonate. The organic phase was diluted with 100 ml of dichloromethane, separated from the aqueous phase, dried over sodium sulfate, and evaporated under reduced pressure. The resulting 5-chloro-3-methylsulfanyl-[1,2,4]triazine-6-carbonitrile was obtained as a brown oil and was used in the following reactions without further purification.

1. temperatureto reflux during 1.5 h
2. temperatureAfter cooling of the dark brown reaction mixture
3. customthe excess of phosphorus oxychloride was evaporated under reduced pressure
4. customTo destroy residues of phosphorus oxychloride
5. dissolutionthe resulting red-brown oily residue was dissolved in 15 ml of toluene
6. additionthe solution added to an ice-cold saturated aqueous solution of sodium hydrogencarbonate
7. additionThe organic phase was diluted with 100 ml of dichloromethane
8. customseparated from the aqueous phase
9. dry with materialdried over sodium sulfate
10. customevaporated under reduced pressure

ORD record

ord-a7294d24228b4c32881799de523d1089

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586422B2