Ethylamine → HCID 23289171, compound

HRID 366330Notes

Reaction equation

HRID 366330 reaction equation
S(Cl)(Cl)=O.[C:5]([C:8]1[O:9][C:10]2[C:16]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])=[CH:15][CH:14]=[C:13]([Cl:30])[C:11]=2[CH:12]=1)([OH:7])=O.[CH2:31]([NH2:33])[CH3:32]>O>[Cl:30][C:13]1[C:11]2[CH:12]=[C:8]([C:5](=[O:7])[NH:33][CH2:31][CH3:32])[O:9][C:10]=2[C:16]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 24386Thionyl Chloride2×HCID 23289196HCID 23289196, compound

Product 1

HCID 23289171HCID 23289171, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of thionyl chloride was added to 0.37 g (0.96 mmol) of 3-(2-carboxy-4-chlorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, followed by stirring for 3 hours under heating and refluxing. After completion of the reaction, thionyl chloride was distilled off under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran. To this solution, 0.24 g (3.84 mmol) of ethylamine (70% aqueous solution) was added, followed by stirring for 10 minutes at room temperature. After completion of the reaction, the reaction solution was poured into water, and precipitated crystals were collected by filtration to obtain 0.31 g (yield: 78.3%) of the desired product as white crystals. Melting point: 225-226° C.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. distillationwas distilled off under reduced pressure
  4. dissolutionThe obtained residue was dissolved in 20 ml of tetrahydrofuran
  5. stirringby stirring for 10 minutes at room temperature
  6. customAfter completion of the reaction
  7. customprecipitated crystals
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-86eeb24a9409484a8e7eba1de6f2f2bd
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

Loading…