Dimethyl Sulfoxide → HCID 13060486, compound

HRID 354868Notes

Reaction equation

HRID 354868 reaction equation
[CH3:1][C:2]1[C:3]([CH3:22])=[CH:4][C:5]2[C:6]3[N:7]([C:12](=[O:21])[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:15]=3)[CH:8]=[N:9][C:10]=2[CH:11]=1.CS(C)=O.[O-:27][CH2:28][CH3:29].[Na+].C(O)C.[Cl-].[NH4+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH3:22][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH3:1])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][CH:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]([O:27][CH2:28][CH3:29])=[O:21]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 13060567HCID 13060567, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 13060486HCID 13060486, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 9,10-dimethyl-4-oxo-4H-primido[1,2-c]quinazoline-3-carboxylate (4.46 g) and anhydrous dimethylsulfoxide (17 ml) was stirred at ambient temperature. To the mixture was dropwise 1 N sodium-ethoxide-ethanol solution (20 ml) and the reaction mixture was stirred for 3 hours at ambient temperature. To the resultant mixture was added ammonium chloride (2.45 g) and the mixture was stirred for 5 minutes. To the mixture was added water and extracted twice with chloroform. After washing three times with water and with aqueous solution saturated with sodium chloride, the combined chloroform layer was treated with activated charcoal, dried over magnesium sulfate and concentrated under reduced pressure to give a residue, which was dissolved in a mixture of chloroform and ethyl acetate. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure and recrystallized twice from ethyl acetate and from a mixture of chloroform and hexane to give diethyl [(6,7-dimethyl-4-quinazolinylamino)methylene]propanedioate (2.01 g).

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at ambient temperature
  2. stirringthe mixture was stirred for 5 minutes
  3. extractionextracted twice with chloroform
  4. washAfter washing three times with water
  5. additionwith aqueous solution saturated with sodium chloride, the combined chloroform layer was treated with activated charcoal
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue, which
  9. customInsoluble materials were removed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customrecrystallized twice from ethyl acetate and from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-f94099a983374d838ad14506f93a5eea
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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