Dicyclohexylcarbodiimide → N-(3-trifluoromethyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide

HRID 543571

반응식

HRID 543571 반응식
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.[F:8][C:9]([F:22])([F:21])[C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[O:17][CH:18]([F:20])[F:19])[NH2:13].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[F:8][C:9]([F:21])([F:22])[C:10]1[CH:11]=[C:12]([NH:13][C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:7])[CH:14]=[CH:15][C:16]=1[O:17][CH:18]([F:19])[F:20]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 813261-Methylcyclopropanecarboxylic acidHCID 204600994-(Difluoromethoxy)-3-(trifluoromethyl)aniline

생성물 1

HCID 13314710N-(3-trifluoromethyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide수율 81.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-methylcyclopropanecarboxylic acid (1.0 g) in tetrahydrofuran (50 ml), 3-trifluoromethyl-4-difluoromethoxyaniline (2.25 g) was added, and a solution of N,N'-dicyclohexylcarbodiimide (DCC) (2.2 g) in tetrahydrofuran was dropwise added while stirring. After several minutes, the by-produced N,N'-dicyclohexylurea (DCU) was eliminated by filtration. To the filtrate, acetic acid (2 ml) was added to decompose excessive DCC, followed by elimination of DCU. The resultant filtrate was extracted with ether, and 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 crude crystals (2.85 g) were recrystallized from ethanol to give N-(3-trifluoromethyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (2.5 g). M.P., 39°-40° C.

후처리

  1. waitAfter several minutes
  2. filtrationthe by-produced N,N'-dicyclohexylurea (DCU) was eliminated by filtration
  3. additionTo the filtrate, acetic acid (2 ml) was added
  4. extractionThe resultant filtrate was extracted with ether
  5. washthe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude crystals (2.85 g) were recrystallized from ethanol

출처 및 근거

ORD 기록
ord-8e274d3e04cd48cb8713b6a544f0a839
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04447260

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