Dimethylformamide → HCID 178486844, compound

HRID 659039Notes

Reaction equation

HRID 659039 reaction equation
CN(C)C=O.[C:6]([C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][N:9]=1)#[N:7].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:20][CH3:21])[N:11]=[CH:10][N:9]=[C:8]2[C:6]1[NH:24][N:23]=[N:22][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59536532HCID 59536532, compound

Product 1

HCID 178486844HCID 178486844, compoundYield 59.16%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

Experimental Procedure: 400.0 ml of dimethyl formamide and 20.0 g (0.09 mol) of 4-cyano-6,7-dimethoxy-quinazoline were charged into a 1.0 L 4necked round bottom flask, connected to a mechanical stirrer, thermometer socket and condenser under nitrogen atmosphere. 6.80 g (0.10 mol) of Sodium azide and 5.50 g (0.10 mol) of ammonium chloride were charged at 25-35° C. Stirred the mass for 15-20 min at 25-35° C. Stirred the mass for 15-20 min at 25-35° C. Reaction mass temperature was raised to 110-115° C. Maintained the mass temperature at 110-115° C. for 8-9 hours. Inorganic solid was filtered at 110-115° C. and the filtrate was collected into a conical flask. Cooled the filtrate to 25-30° C. 4000.0 ml of ethyl acetate was charged into a 5.0 L 4necked round bottom flask, connected to a mechanical stirrer, thermometer socket and addition flask. Reaction mass of dimethyl formamide solution was added to ethyl acetate solution under stirring. Maintained the mass temperature at 25-30° C. for 60-90 min. Cooled the mass temperature to 0-5° C. Maintained the mass temperature at 0-5° C. for 150-180 min. Filtered the solid and solid was washed with 100.0 ml of ethyl acetate. Compound was dried at 25-30° C. under vacuum. Obtained 14.20 g (yield is 59.16% by theory) of product Melting range 207.2° C.

Workup

  1. customconnected to a mechanical stirrer
  2. stirringStirred the mass for 15-20 min at 25-35° C
  3. customReaction mass temperature
  4. temperaturewas raised to 110-115° C
  5. temperatureMaintained the mass temperature at 110-115° C. for 8-9 hours
  6. filtrationInorganic solid was filtered at 110-115° C.
  7. customthe filtrate was collected into a conical flask
  8. temperatureCooled the filtrate to 25-30° C
  9. addition4000.0 ml of ethyl acetate was charged into a 5.0 L 4necked round bottom flask
  10. customconnected to a mechanical stirrer
  11. additionthermometer socket and addition flask
  12. customReaction mass of dimethyl formamide solution
  13. stirringunder stirring
  14. temperatureMaintained the mass temperature at 25-30° C. for 60-90 min
  15. temperatureCooled the mass temperature to 0-5° C
  16. temperatureMaintained the mass temperature at 0-5° C. for 150-180 min
  17. filtrationFiltered the solid and solid
  18. washwas washed with 100.0 ml of ethyl acetate
  19. customCompound was dried at 25-30° C. under vacuum

Sources & evidence

ORD record
ord-d79cd0d65e164465a4ec8e11c16b1495
Source dataset
uspto-grants-2011_12
Patent number
US08080558B2

Reaction notes

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