Sulfuric Acid → 7-Methoxy-1-methyl-5-phenyl[1,2,4]triazolo[4,3-a]quinazoline

HRID 1414892Notes

Reaction equation

HRID 1414892 reaction equation
[NH:1]([C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:19][CH3:20])[CH:9]=2)[N:4]=1)[NH2:2].[C:21]([O-])([O-])(OCC)[CH3:22].S(=O)(=O)(O)O>C(O)C>[CH3:21][C:22]1[N:4]2[C:5]3[C:10]([C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:12][C:3]2=[N:1][N:2]=1)=[CH:9][C:8]([O:19][CH3:20])=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21485896HCID 21485896, compoundHCID 86598186Ethyl ortho-acetate

Product 1

HCID 214859287-Methoxy-1-methyl-5-phenyl[1,2,4]triazolo[4,3-a]quinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the next place, to a solution of 2.0 g of 2-hydrazino-4-phenyl-6-methoxyquinazoline in 100 ml of ethanol were added 3.5 g of ethyl orthoacetate and 0.5 ml of concentrated sulfuric acid. The resulting mixture was refluxed for 3 hours and then the solvent was removed under reduced pressure. To the residue was added ammonia water to basify, and the mixture was extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness in vacuo. To the residue was added ethanol and the crystallized product was collected by filtration, and dried to give 1-methyl-5-phenyl-7-methoxy-s-triazolo[4,3-a]quinazoline as slightly yellow needles, m.p. 251° - 252° C.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. customthe solvent was removed under reduced pressure
  3. additionTo the residue was added ammonia water
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness in vacuo
  8. additionTo the residue was added ethanol
  9. filtrationthe crystallized product was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-074cbc054fa3473bb10d7cba46b99324
Source dataset
uspto-grants-1977_01
Patent number
US04002755

Reaction notes

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