Oxalyl chloride → 1-allyl-3,5-dichloro-6-methylpyrazin-2(1H)-one
Reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[ClH:7].[CH2:8]([NH:11][CH:12]([CH3:15])[C:13]#[N:14])[CH:9]=[CH2:10]>ClC1C=CC=CC=1Cl>[CH2:8]([N:11]1[C:12]([CH3:15])=[C:13]([Cl:7])[N:14]=[C:1]([Cl:6])[C:2]1=[O:3])[CH:9]=[CH2:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A stirred mixture of oxalyl chloride (30.5 ml, 0.35 mol) and α-(allylamino)-propionitrile hydrochloride (10.26 g, 70 mmol) in o-dichlorobenzene (100 ml) was heated to 100° C. for 15 h. The solvent was evaporated in vacuo and the residual black oil was purified by flash column chromatography on silica (eluting with 30% ethyl acetate hexanes) to give the title compound as a tan crystalline solid:
Workup
- customThe solvent was evaporated in vacuo
- customthe residual black oil was purified by flash column chromatography on silica (eluting with 30% ethyl acetate hexanes)
Sources & evidence
- ORD record
- ord-929d9cd804db4288ba9afabd3d0fb51e
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866573
Reaction notes
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