Triethylamine → 2,2-difluoro-N-methoxy-N-methylcyclopropane-1-carboxamide

HRID 561445Notes

Reaction equation

HRID 561445 reaction equation
[F:1][C:2]1([F:8])[CH2:4][CH:3]1[C:5](Cl)=[O:6].FF.Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C>ClCCl.O>[F:1][C:2]1([F:8])[CH2:4][CH:3]1[C:5]([N:13]([O:14][CH3:15])[CH3:12])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24524FluorineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 150990752,2-Difluorocyclopropane-1-carbonyl chloride

Product 1

HCID 534161312,2-difluoro-N-methoxy-N-methylcyclopropane-1-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7.00 g (49.8 mmol) of 2,2-difluorocyclopropanecarbonyl chloride (described in the Journal of Fluorine Chemistry 1990, 49, 127-139) in 100 ml of dichloromethane were mixed with 6.32 g (64.8 mmol) of N,O-dimethylhydroxylamine hydrochloride and 18.1 ml (130 mmol) of triethylamine and stirred at RT overnight. Water was added to the reaction mixture, the phases were separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. 5.73 g (70% of theory) of the title compound were obtained and were reacted without further purification.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-481566167d8947818e363c2f0c197f81
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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