Hydrogen Peroxide → HCID 11976498, compound

HRID 736447Notes

Reaction equation

HRID 736447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([C:12]#[N:13])[CH2:11][CH2:10]1.[OH-:14].[Na+].OO>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([C:12]([NH2:13])=[O:14])[CH2:10][CH2:11]1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 149962871-(2,6-Difluorophenyl)cyclopropanecarbonitrile

Product 1

HCID 11976498HCID 11976498, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2,6-Difluorophenyl)cyclopropanecarbonitrile (5.42 g) was hydrolyzed at ambient temperature with an aqueous solutions of 5N sodium hydroxide (20 mL), 55% tetrabutylammonium hydrogensulfate (0.5 mL) and 30% hydrogen peroxide (5 mL) in toluene (5 mL) for 39 hours. The prepared semi-solid reaction mixture was diluted with ethyl acetate and the phases were separated. The aqueous phase was neutralized with 5% hydrochloric acid and extracted twice with ethyl acetate. The combined organic extracts were washed with 5% hydrochloric acid, then brine, and dried over anhydrous sodium sulfate. Filtration and evaporation gave 1-(2,6-difluorophenyl)cyclopropanecarboxylic acid amide as light-brown solid (4.98 g, 84% yield). M.p. 136.7-137.6° C. (from ethyl acetate). GC/MS: m/z 197 (purity 97.5%, RT 9.85 min.). 1H-NMR (DMSO-d6): δ 7.43-7.34 (m, 1H), 7.10-7.01 (m, 2H), 6.96 (br s, 1H), 6.64 (br s, 1H), 1.50-1.46 (m, 2H), 1.00-0.97 (m, 2H). 1H-NMR (CDCl3): δ 7.61-7.26 (m, 1H), 6.98-6.90 (m, 2H), 5.44 (br s, 2H), 1.79-1.74 (m, 2H), 1.17-1.12 (m, 2H). 13C-NMR (DMSO-d6): 173.4, 164.2, 160.9, 130.3, 116.5, 112.1, 19.05, 15.8.

Workup

  1. customThe prepared semi-solid reaction mixture
  2. customthe phases were separated
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with 5% hydrochloric acid
  5. dry with materialbrine, and dried over anhydrous sodium sulfate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-59eff49a8d8640758a2f6ee0070b73d4
Source dataset
uspto-grants-2009_09
Patent number
US07595338B2

Reaction notes

Loading…