Acetonitrile, 2,2-diethoxy- → HCID 58764230, compound
Reaction equation
C[O-].[Na+].[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8]#[N:9])[CH3:5].Cl.[CH3:14][NH:15][N:16]=[C:17](N)[CH2:18][CH3:19].C([O-])(=O)C.[Na+]>CO>[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8]1[N:15]([CH3:14])[N:16]=[C:17]([CH2:18][CH3:19])[N:9]=1)[CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of sodium methoxide (3.30 g, 0.0611 mol) in methanol (100 mL) was added at room temperature to a solution of diethoxyacetonitrile (78.9 g, 0.611 mol) in methanol (600 mL). The resulting mixture was stirred at room temperature overnight, and a solution of crude N′-methylpropanehydrazonamide hydrochloride from Step 2 (84.1 g, ˜0.60 mol) in methanol (200 mL) was added. Anhydrous sodium acetate (50.0 g, 0.61 mol) was added, and the resulting mixture was refluxed under an atmosphere of Ar for 20 h. Then methanol was evaporated, and the dark oily residue was extracted with ether (3×250 mL). The ether solution was passed through a layer of silica gel, and the filtrate was evaporated. The residue was distilled in vacuo to give 35.0 g (27%) of the title product (bp 68° C. at 0.1 mm Hg). Note: There is a higher-boiling second fraction (15 g; bp 120° C. at 0.1 mm Hg) that is a triazole impurity containing two acetal groups.
Workup
- temperaturethe resulting mixture was refluxed under an atmosphere of Ar for 20 h
- customThen methanol was evaporated
- extractionthe dark oily residue was extracted with ether (3×250 mL)
- customthe filtrate was evaporated
- distillationThe residue was distilled in vacuo
Sources & evidence
- ORD record
- ord-bcb42a80ae7f4272b91148dcd40ec41c
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268835B2
Reaction notes
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