Water → N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide

HRID 543574Notes

Reaction equation

HRID 543574 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([F:12])[F:11])[NH2:5].C(N(CC)CC)C.[CH3:20][C:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.O>C(Cl)Cl>[F:12][CH:10]([F:11])[O:9][C:8]1[CH:7]=[CH:6][C:4]([NH:5][C:24]([C:21]2([CH3:20])[CH2:23][CH2:22]2)=[O:25])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 132929114-(Difluoromethoxy)-3-fluoroaniline

Product 1

HCID 13314707N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamideYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-fluoro-4-difluoromethoxyaniline (1.8 g) in methylene chloride (50 ml), triethylamine (1.1 g) was added, and a solution of 1-methylcyclopropanecarbonyl chloride (1.2 g) in methylene chloride was dropwise added thereto while stirring and ice-cooling. After stirring at room temperature for 1 hour, the reaction mixture was admixed with water and extracted with ether. The extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The oily residue (2.5 g) was chromatographed on silica gel and eluted with a mixture of hexane and acetone to give N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide (2.2 g). nD24 1.5061.

Workup

  1. temperatureice-cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. extractionextracted with ether
  4. washThe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe oily residue (2.5 g) was chromatographed on silica gel
  8. washeluted with a mixture of hexane and acetone

Sources & evidence

ORD record
ord-98c32e5879324ad5b230caa78cffee18
Source dataset
uspto-grants-1984_05
Patent number
US04447260

Reaction notes

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