Dimethylformamide → 4-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrile

HRID 47061

반응식

HRID 47061 반응식
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:14])[CH:12]=O>>[CH3:10][N:11]([CH3:14])[CH:12]=[CH:1][C:2]1[CH:3]=[CH:4][N:5]=[CH:6][C:7]=1[C:8]#[N:9]

참가 물질

3

반응물 2

HCID 6228DimethylformamideHCID 2278064-Methyl-3-cyanopyridine

생성물 1

HCID 543988174-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrile수율 63%

실험 절차

A solution of 4-methylnicotinonitrile (13.8 g, 0.12 m), dimethylformamide (DMF) (100 mL) and DMF acetal (14.0 g, 0.12 m) was heated at reflux under N2. After 16 hours, the reaction mixture was concentrated at atmospheric pressure until the internal temperature reached 150°. The mixture was then cooled, poured into H2O (1 L) and extracted with C6H6 (6×200 mL). The combined organic extracts were washed with H2O (2×200 mL), dried, filtered and evaporated to dryness. The residue was distilled at 150°-160° (0.2 mm) to yield 12.6 g (63%) of N,N-dimethyl-2-(3-cyano-4-pyridyl)ethenamine. An analytical sample was prepared by crystallization from C6H6 --C6H14, mp 88°-90°.

후처리

  1. temperatureat reflux under N2
  2. concentrationthe reaction mixture was concentrated at atmospheric pressure until the internal temperature
  3. customreached 150°
  4. temperatureThe mixture was then cooled
  5. additionpoured into H2O (1 L)
  6. extractionextracted with C6H6 (6×200 mL)
  7. washThe combined organic extracts were washed with H2O (2×200 mL)
  8. customdried
  9. filtrationfiltered
  10. customevaporated to dryness
  11. distillationThe residue was distilled at 150°-160° (0.2 mm)

출처 및 근거

ORD 기록
ord-6dbade8656ef4e5db9489c5be0401d9d
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04176183

연결된 노트

불러오는 중…