Pyridine → Benzamide, 4-nitro-N-2-propynyl-

HRID 880488노트

반응식

HRID 880488 반응식
Cl.[CH2:2]([NH2:5])[C:3]#[CH:4].N1C=CC=CC=1.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]>O1CCCC1>[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:5][CH2:2][C:3]#[CH:4])=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 11205720Prop-2-ynylamine hydrochloride

생성물 1

HCID 3016782Benzamide, 4-nitro-N-2-propynyl-수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of propargylamine hydrochloride (5.0 g, 54.6 mmol) and pyridine (7.8 g, 99.1 mmol) in tetrahydrofuran (30 mL) was added 4-nitro-benzoylchloride (9.2 g, 49.6 mmol) in tetrahydrofuran (20 mL) and the mixture was heated at reflux for 16 h. The mixture was allowed to cool to ambient temperature and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford 4-nitro-N-prop-2-ynyl-benzamide (7.74 g, 77%) as a solid.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate solution, water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-82444f68bda74462823d049127359f81
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

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