Triethylamine → N-methoxy-N,2-dimethylcyclopropane-1-carboxamide
Reaction equation
[CH3:1][CH:2]1[CH2:4][CH:3]1[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)CC)C>C1C=CC=CC=1.CN(C)C=O>[CH3:18][O:17][N:16]([CH3:15])[C:5]([CH:3]1[CH2:4][CH:2]1[CH3:1])=[O:7]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-methylcyclopropanecarboxylic acid (10 g in a mixture of 200 mL benzene and 2 mL N,N-dimethylformamide) at 0° C. was added 10.5 mL of oxalyl chloride and the mixture stirred at 0° C. for 30 minutes then warmed to room temperature for 30 minutes. At this time, 14.6 g of N,O-dimethylhydroxylamine hydrochloride was added followed by 41 mL of triethylamine. The mixture was stirred at room temperature for one hour then quenched by the addition of saturated sodium bicarbonate. The aqueous portion was extracted with ethyl acetate and the combined organics washed with brine, dried over sodium sulfate and concentrated in vacuo. The product was purified by distillation under reduced pressure to give 8.9 g as an oil.
Workup
- temperaturethen warmed to room temperature for 30 minutes
- stirringThe mixture was stirred at room temperature for one hour
- customthen quenched by the addition of saturated sodium bicarbonate
- extractionThe aqueous portion was extracted with ethyl acetate
- washthe combined organics washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- distillationThe product was purified by distillation under reduced pressure
- customto give 8.9 g as an oil
Sources & evidence
- ORD record
- ord-3f71ed3a8c694a839f75b3d5a8ee910e
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849764
Reaction notes
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