Phosphorus oxychloride → HCID 68678410, compound
Reaction equation
[C:1]([N:5]1[C:18](=[O:19])[N:8]2[CH:9]=[C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[NH:11][C:12](=O)[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[C:1]([N:5]1[C:18](=[O:19])[N:8]2[CH:9]=[C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:11]=[C:12]([Cl:22])[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
A solution of 5.90 g the product of Step D in phosphoryl chloride (100 mL) was heated to 110° C. After 16 h, the reaction mixture was cooled and the excess phosphoryl chloride was removed by distillation at reduced pressure (15 mm Hg). The residue was dissolved in chloroform and carefully poured onto 200 g of ice. After the ice had melted, the layers were separated and the aqueous was extracted with chloroform. The combined organic layers were washed with sat. sodium chloride solution, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to yield 2-tert-butyl-8-chloro-6-tert-butyl-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one as a yellow solid. MS (M+H+)=283.3.
Workup
- temperaturethe reaction mixture was cooled
- customthe excess phosphoryl chloride was removed by distillation at reduced pressure (15 mm Hg)
- dissolutionThe residue was dissolved in chloroform
- additioncarefully poured onto 200 g of ice
- customthe layers were separated
- extractionthe aqueous was extracted with chloroform
- washThe combined organic layers were washed with sat. sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-f00ce380245e4616be43c32ed5237883
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709473B2
Reaction notes
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