Triethylamine → N-Methoxy-N-methylcyclopropanecarboxamide

HRID 898116Notes

Reaction equation

HRID 898116 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1>C(Cl)Cl>[CH3:5][O:4][N:3]([CH3:2])[C:16]([CH:13]1[CH2:15][CH2:14]1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 15643267N-Methoxy-N-methylcyclopropanecarboxamideYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,O-dimethyl-hydroxylamine HCl (40 g, 410 mmol) was suspended under nitrogen in DCM (400 mL) and cooled in ice. Triethylamine (63 mL, 451 mmol) was added slowly, then cyclopropanecarbonyl chloride (41 mL, 451 mmol) was added slowly. Stirring without cooling was continued for 1 h. Extraction: 2×DCM, 1×1 N HCl, 1×NaCl. Distillation: 75° C./20 mbar. One obtained 32.5 g (61%) of a colorless oil.

Workup

  1. temperaturecooled in ice
  2. temperaturewithout cooling
  3. extractionExtraction
  4. distillationDistillation
  5. custom75° C./20 mbar

Sources & evidence

ORD record
ord-7c669845a24a43bb8a9dda151da4a71a
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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