Allyl Alcohol → N,N-Dimethyl-3-[(prop-2-en-1-yl)oxy]pyrazin-2-amine
Reaction equation
Cl[C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([OH:14])[CH:12]=[CH2:13].[H-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:11]([O:14][C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[N:6][CH:5]=[CH:4][N:3]=1)[CH:12]=[CH2:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
47 g of 2-chloro-3-dimethylamino-pyrazine and 35 g of allyl alcohol are dissolved in 300 ml of hexamethylphosphoric acid triamide. 14.4 g of sodium hydride are introduced into this solution at 0° C. over the course of 30 minutes. The mixture is then stirred for a further hour at 0° C. and for 15 hours at room temperature. The reaction mixture is then poured into 2 liters of ice water. After excess sodium hydride has been decomposed, the mixture is extracted by shaking with ether. The ether extracts are washed with water until neutral, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue is distilled under reduced pressure. 2-Allyloxy-3-dimethylamino-pyrazine, boiling point 110°-115° C./10 mm Hg, is thus obtained.
Workup
- extractionthe mixture is extracted
- stirringby shaking with ether
- washThe ether extracts are washed with water until neutral,
- dry with materialdried over sodium sulphate
- customevaporated in a waterpump vacuum
- distillationThe residue is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-42943661e90d446f857b2d56334a17b6
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04115575
Reaction notes
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