Pyridine → 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline

HRID 1649365노트

반응식

HRID 1649365 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[NH:4][CH2:5][C:6]#[CH:7].N1C=CC=CC=1.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25]>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[N:4]([C:24]([C:20]1[O:19][CH:23]=[CH:22][CH:21]=1)=[O:25])[CH2:5][C:6]#[CH:7]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 2997052,6-dimethyl-N-prop-2-ynyl-aniline

생성물 1

HCID 131504722,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

15.9 g (0.1 mol) of 2,6-dimethyl-N-propargylaniline and 8 g (0.1 mol) of pyridine were heated to the boil in 100 ml of tetrahydrofuran, and 13 g (0.1 mol) of furan-2-carboxylic acid chloride were added carefully. The reaction mixture was stirred under reflux for 15 minutes and then concentrated by distilling off the solvent in vacuo. The residue was taken up in methylene chloride and the methylene chloride mixture was washed with water. The organic phase was separated off, dried over sodium sulphate and concentrated. After triturating with petroleum ether, the residue crystallized. 22.5 g (89% of theory) of 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline of melting point 109°-112° C. were obtained.

후처리

  1. temperatureunder reflux for 15 minutes
  2. concentrationconcentrated
  3. distillationby distilling off the solvent in vacuo
  4. washthe methylene chloride mixture was washed with water
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customAfter triturating with petroleum ether
  9. customthe residue crystallized

출처 및 근거

ORD 기록
ord-9a21761f63484d8faa5693dd9f8d5258
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04416889

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