Pivalic acid → HCID 58088199, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)#[N:2].[C:9](O)(=O)[C:10](C)([CH3:12])[CH3:11].[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O>[N+]([O-])([O-])=O.[Ag+]>[C:10]([C:6]1[N:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=1)([CH3:12])([CH3:11])[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To an aqueous (1.5 L) solution of 2-cyanopyrazine (60 g), pivalic acid (56 mL) and ammonium peroxodisulfate (100 g) were added, then silver nitrate (146 g) was added, and the resultant was stirred at 80° C. for 2.5 hours. The reaction solution was extracted with ethyl acetate. Ethyl acetate was further added to the extract, and the suspension was filtered. Saturated saline was added to the filtrate, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified twice by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→50/50) to obtain the title compound (54 g) as a pale yellow solid.
Workup
- extractionThe reaction solution was extracted with ethyl acetate
- additionEthyl acetate was further added to the extract
- filtrationthe suspension was filtered
- additionSaturated saline was added to the filtrate
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationthe desiccant was filtered off
- distillationThen, the solvent was distilled off under reduced pressure
- customThe obtained residue was purified twice by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→50/50)
Sources & evidence
- ORD record
- ord-b476e79dbeca4cf3a863646bc18fe554
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045466B2
Reaction notes
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