Triethylamine → N-[2-[2-Cyanophenoxy]phenyl]-4-hexyloxybenzamide

HRID 1609269

반응식

HRID 1609269 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].C(N(CC)CC)C.[CH2:24]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CCOCC>[C:7]([C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[NH:1][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=1)#[N:8]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-HCID 200843882-(2-Aminophenoxy)benzonitrile

생성물 1

HCID 20084541N-[2-[2-Cyanophenoxy]phenyl]-4-hexyloxybenzamide수율 77.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

In 20 ml of ether was dissolved 2.0 g of 2-(2-aminophenoxy)benzonitrile followed by addition of 2.04 g of triethylamine. Then, with ice-cooling and stirring, a solution of 2.67 g of 4-hexyloxybenzoyl chloride in 5 ml of ether was added dropwise. The mixture was further stirred at the same temperature for 1 hour. The reaction mixture was then washed with diluted hydrochloric acid and aqueous sodium hydrogen carbonate solution in that order, dried and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate-n-hexane as the eluent and the relevant fraction was crystallized from diisopropyl ether to give 3.05 g of the title compound as white crystals.

후처리

  1. temperatureThen, with ice-cooling
  2. stirringThe mixture was further stirred at the same temperature for 1 hour
  3. washThe reaction mixture was then washed with diluted hydrochloric acid and aqueous sodium hydrogen carbonate solution in that order
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customthe relevant fraction was crystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-5b022dcb1f1d4d9ba8c88d9364ccec6c
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05399703

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