Triethylamine → HCID 13314711, compound

HRID 543573Notes

Reaction equation

HRID 543573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11])[NH2:5].C(N(CC)CC)C.[CH3:21][C:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:25]([C:22]2([CH3:21])[CH2:24][CH2:23]2)=[O:26])[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27738433-Chloro-4-(trifluoromethoxy)anilineHCID 127899391-Methylcyclopropane-1-carbonyl chloride

Product 1

HCID 13314711HCID 13314711, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-chloro-4-trifluoromethoxyaniline (2.1 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 washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The crude crystals (2.9 g) were recrystallized from ethanol to give N-(3-chloro-4-trifluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (2.6 g). M.P., 101°-102° C.

Workup

  1. temperatureice-cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. washthe reaction mixture was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude crystals (2.9 g) were recrystallized from ethanol

Sources & evidence

ORD record
ord-faa184fb958d49239921cbe6c9a76367
Source dataset
uspto-grants-1984_05
Patent number
US04447260

Reaction notes

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