(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanone → beta-Dimethylamino-1-(2-thienyl)-2-propen-1-one

HRID 2184798노트

반응식

HRID 2184798 반응식
N[C:2]1[C:6]([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])=CNN=1.[CH3:14][N:15](C)[CH:16]=CC(C1C=C(N(C)C(=O)C)C=CC=1)=O>C(O)(=O)C>[CH3:14][N:15]([CH3:16])[C:6](=[CH2:2])[C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8]

참가 물질

4

반응물 2

HCID 11550150(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanoneHCID 53424451N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide

생성물 1

HCID 22288452beta-Dimethylamino-1-(2-thienyl)-2-propen-1-one수율 70%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of (3-amino-1H-pyrazol-4-yl)-2-thienylmethanone (4) (1.93 g, 10 mmol) and N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (6) (2.46 g, 10 mmol) in glacial acetic acid (100 mL) is refluxed for 8 hrs. Evaporation of all volatiles on a rotary evaporator gives a residue which is partitioned between aqueous saturated sodium bicarbonate and methylene chloride. The methylene chloride layer is dried over sodium sulfate and filtered. Two additional volumes of methylene chloride are added and the solution is warmed to reflux. Hexane is added until crystallization is observed. The mixture is cooled and filtered to give Compound 1 as a yellow solid (2.57 g, 7 mmol, 70%).

후처리

  1. temperatureis refluxed for 8 hrs
  2. customEvaporation of all volatiles
  3. customon a rotary evaporator
  4. customgives a residue which
  5. customis partitioned between aqueous saturated sodium bicarbonate and methylene chloride
  6. dry with materialThe methylene chloride layer is dried over sodium sulfate
  7. filtrationfiltered
  8. additionTwo additional volumes of methylene chloride are added
  9. temperaturethe solution is warmed to reflux
  10. additionHexane is added until crystallization
  11. temperatureThe mixture is cooled
  12. filtrationfiltered

출처 및 근거

ORD 기록
ord-639ca7738a334b5da05fbe243ad09591
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399621B1

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