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

HRID 880488ノート

反応式

HRID 880488 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82444f68bda74462823d049127359f81
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

反応ノート

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