Cyclopropanecarbonyl chloride → N-Methoxy-N-methylcyclopropanecarboxamide

HRID 2206596Notes

Reaction equation

HRID 2206596 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH:6]1([C:9](Cl)=[O:10])[CH2:8][CH2:7]1>C(Cl)Cl>[CH3:5][O:4][N:3]([CH3:2])[C:9]([CH:6]1[CH2:8][CH2:7]1)=[O:10]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 15643267N-Methoxy-N-methylcyclopropanecarboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

N,O-dimethylhydroxylamine hydrochloride (11.2 g, 114.79 mmol) and TEA (19.36 g, 191.32 mmol) were dissolved in CH2Cl2 (60 ml). Cyclopropanecarbonyl chloride (10 g, 95.66 mmol) was added dropwise at 0° C. After addition, the mixture was allowed to warm to 25° C. and stirred for 18 h. After the reaction completed, the solution was washed with H2O, saturated NaHCO3, 1 N HCl and brine. The organic layer was dried over Na2SO4 and evaporated under reduced pressure to get N-methoxy-N-methylcyclopropanecarboxamide as a yellow oil. (8.6 g, yield 70%).

Workup

  1. additionAfter addition
  2. washthe solution was washed with H2O, saturated NaHCO3, 1 N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b302906ed9324ff3ac4dac0949700cd5
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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