Magnesium orthosilicate → 7-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1707059Notes

Reaction equation

HRID 1707059 reaction equation
[CH3:1][N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[NH2:14][C:15]1N=C[NH:17][N:16]=1.C(=O)(O)[O-].[Na+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(Cl)Cl.CCCCCC.C(O)(=O)C>[C:7]1([C:5]2[N:17]3[N:16]=[CH:15][N:14]=[C:1]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 66225Magnesium orthosilicateHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 516892Sodium BicarbonateHCID 178418311HCID 178418311, compound

Product 1

HCID 9009307-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A mixture of 5.25 g. of 3-dimethylaminoacrylophenone and 2.52 g. of 3-amino-1,2,4-triazole in 25 ml. of glacial acetic acid is refluxed for 4 hours. Evaporation gives a solid which is treated with a saturated sodium bicarbonate solution and dissolved in methylene chloride. This solution is passed through a short column of a hydrous magnesium silicate. Addition of hexane to a refluxing solution of the eluent gives crystals of the desired compound, m.p. 143°-144° C. K. Shirakawa, Yakugaku Zasshi 80, 956 (1960) cites melting point 140° C. for the compound assigned this structure but prepared by a different route.

Workup

  1. additionA mixture of 5.25 g
  2. customEvaporation
  3. customgives a solid which

Sources & evidence

ORD record
ord-a58cc36475914bf4bf31323d18a9e0e2
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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