Propargylamine → 4-propargylamino-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

HRID 639740Notes

Reaction equation

HRID 639740 reaction equation
CO[C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]#[N:23])[CH:15]=1.[CH2:25]([NH2:28])[C:26]#[CH:27]>C1C=CC=CC=1>[CH2:25]([NH:28][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]#[N:23])[CH:15]=1)[C:26]#[CH:27]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 686765464-methoxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

Product 1

HCID 740199984-propargylamino-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-oneYield 31.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 0.20 g of 4-methoxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one and 10 ml of benzene was added 34.3 mg of propargylamine, and the mixture was heated under refluxing for 3 hours and 45 minutes. After cooling to room temperature, precipitated crystals were filtered to obtain 68.0 mg of 4-propargylamino-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (20b)] as a pale brown powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 3 hours and 45 minutes
  3. customprecipitated crystals
  4. filtrationwere filtered

Sources & evidence

ORD record
ord-249f955ad78642aa97d8afc7ae3eed9f
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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