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

HRID 2184798Notes

Reaction equation

HRID 2184798 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-639ca7738a334b5da05fbe243ad09591
Source dataset
uspto-grants-2002_06
Patent number
US06399621B1

Reaction notes

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