Hydrochloric Acid → HCID 21094273, compound

HRID 1350071Notes

Reaction equation

HRID 1350071 reaction equation
[CH:1]([NH:3][CH2:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.P(Cl)(Cl)([Cl:24])=O.Cl>C(#N)C.C(O)C.CCOCC>[ClH:24].[CH3:21][O:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[CH:1]=[N:3][CH2:4][CH:5]2[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 21094280HCID 21094280, compound

Product 1

HCID 21094273HCID 21094273, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

The formaldehyde obtained in Step C (6.8 g; 23 mmol) is dissolved in 100 ml of acetonitrile, then the reaction mixture is heated to approximately 60° C. Phosphorus oxychloride (7 ml) is added to the solution, which is heated at reflux for 6 hours with stirring and then evaporated under reduced pressure. The residue obtained is taken up twice in ethanol and evaporated under reduced pressure, and is then taken up in water. The aqueous phase is washed with dichloromethane and then rendered alkaline with a saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oil obtained is taken un in ether saturated with HCl(g) and then evaporated under reduced pressure. The residue is taken up in toluene in the heated state and is stirred until precipitation occurs. The precipitate obtained is then suction-filtered off and the title product is obtained in the form of a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. customevaporated under reduced pressure
  4. customThe residue obtained
  5. customevaporated under reduced pressure
  6. washThe aqueous phase is washed with dichloromethane
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase is dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe oil obtained
  12. customevaporated under reduced pressure
  13. stirringis stirred until precipitation
  14. customThe precipitate obtained
  15. filtrationis then suction-filtered off

Sources & evidence

ORD record
ord-23773840efa247cf9a7053658010a93e
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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