Methylamine → HCID 11448282, compound

HRID 1350086Notes

Reaction equation

HRID 1350086 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[C:7]2[CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=O.[CH3:22][NH2:23]>O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[C:7]2[CH2:14][CH2:15][CH2:16][C:17]([NH:23][CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21094275HCID 21094275, compound

Product 1

HCID 11448282HCID 11448282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound obtained in Step A (2.2 g; 7 mmol) is dissolved in 30 ml of methylamine (40% in water) and the mixture is heated at reflux for 3 hours with stirring. The reaction mixture is taken up in 50 ml of water and extracted with ether. The organic phase is washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oil obtained is purified by chromatography on silica gel (eluant: dichloromethane with the progressive addition of methanol). The oil obtained is evaporated under reduced pressure and the precipitate so formed is recrystallised from toluene to yield the title product in the form of a white solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe oil obtained
  9. customis purified by chromatography on silica gel (eluant
  10. additiondichloromethane with the progressive addition of methanol)
  11. customThe oil obtained
  12. customis evaporated under reduced pressure
  13. customthe precipitate so formed
  14. customis recrystallised from toluene

Sources & evidence

ORD record
ord-c9b8ab64e90e4d5e86dd2c1ceffb6c19
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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