Triethylamine → 4-Bromo-N-(3-iodo-phenyl)-butyramide

HRID 82044

반응식

HRID 82044 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[Br:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>ClCCl.C1CCCCC1.CCOCC>[Br:16][CH2:17][CH2:18][CH2:19][C:20]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=1)=[O:21]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 122713-IodoanilineHCID 702254-Bromobutyryl chloride

생성물 1

HCID 866781774-Bromo-N-(3-iodo-phenyl)-butyramide수율 64%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8078Cyclohexane용매

실험 절차

To a solution of 3-iodoaniline (1.5 g, 6.85 mmol) and triethylamine (1.34 mL, 9.59 mmol) in dichloromethane (28 mL) at 0° C. was added dropwise 4-bromobutyryl chloride (0.99 mL, 8.56 mmol). The reaction mixture was then stirred at room temperature overnight. The organic extract was washed with an aqueous 1M HCl solution, aqueous 1M NaOH solution and brine, dried (Na2SO4), filtered, concentrated under vacuum. The crude residue was purified by silica gel column chromatography using a gradient of EtOAc (0-15%) in cyclohexane to yield a sticky solid. Trituration in a mixture of cyclohexane and ether and then filtration give the title compound as a solid (1.61 g, 64%).

후처리

  1. extractionThe organic extract
  2. washwas washed with an aqueous 1M HCl solution, aqueous 1M NaOH solution and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified by silica gel column chromatography
  7. customto yield a sticky solid
  8. filtrationfiltration

출처 및 근거

ORD 기록
ord-f7871a57384f4a538967d51a3894c02f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846712B2

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