Water → N-(3-chloro-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide

HRID 543568Notes

Reaction equation

HRID 543568 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:24]([C:21]2([CH3:20])[CH2:23][CH2:22]2)=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([F:11])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20641533-Chloro-4-(difluoromethoxy)anilineHCID 127899391-Methylcyclopropane-1-carbonyl chloride

Product 1

HCID 13042227N-(3-chloro-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-chloro-4-difluoromethoxyaniline (1.95 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 while cooling with ice-water. The reaction mixture was stirred at room temperature for 1 hour, 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 to give crude crystals (2.6 g). Recrystallization from ethanol gave N-(3-chloro-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (2.2 g). M.P., 59°-60° C.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give crude crystals (2.6 g)
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f0bb98829a8d41b3b6b429fdd9150e09
Source dataset
uspto-grants-1984_05
Patent number
US04447260

Reaction notes

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