1,2-Dichloroethane → N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

HRID 216311Notes

Reaction equation

HRID 216311 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[F:6][C:7]([F:15])([F:14])[C:8]1([C:11](O)=[O:12])[CH2:10][CH2:9]1.C(Cl)CCl.O.OC1C2N=NNC=2C=CC=1.CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C>[CH3:5][O:4][N:3]([CH3:2])[C:11]([C:8]1([C:7]([F:15])([F:14])[F:6])[CH2:10][CH2:9]1)=[O:12]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 57785368N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,O-Dimethylhydroxylamine hydrochloride (7.17 g, 73.5 mmol) was added to an ambient temperature solution of 1-trifluoromethylcyclopropane-1-carboxylic acid (10.3 g, 66.8 mmol), EDC (15.4 g, 80.2 mmol), hydroxybenzotriazole hydrate (12.28 g, 80.2 mmol) and N-methylmorpholine (36.7 mL, 33.8 mmol) in methylene chloride (50 mL) at ambient temperature. After stirring at ambient temperature overnight, the reaction mixture was poured into ethyl acetate and washed successively with 2 M hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated to afford N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide which was used in the subsequent step without further purification.

Workup

  1. washwashed successively with 2 M hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-91e68a494d0341eb866aaadb1993f4ba
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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