p-Toluenesulfonic acid → 5-Chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline

HRID 972713Notes

Reaction equation

HRID 972713 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([Cl:15])[N:7]=[C:6]2[NH:16][NH2:17].[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.COC(OC)OC>>[Cl:15][C:8]1[N:7]2[CH:18]=[N:17][N:16]=[C:6]2[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 640302-Chloro-4-hydrazino-6,7-dimethoxyquinazoline

Product 1

HCID 214051435-Chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline

Procedure

A mixture of 10.0 g. of 6,7-dimethoxy-2-chloro-4-hydrazinoquinazoline, 1.0 g. of p-toluenesulfonic acid and 150 ml. of trimethoxy methane is refluxed with stirring for 19 hours and then stirred for 24 hours at room temperature. The resulting mixture is evaporated in vacuo to dryness and the residue dissolved in 1500 ml. of methylene chloride. This solution is extracted twice with sodium carbonate solution, washed neutral with water, dried and evaporated in vacuo to dryness. The residue is twice crystallized from methylene chloride/ diethyl ether and then from ethanol to obtain 5-chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline, m.p. 269°-271° C.

Workup

  1. additionA mixture of 10.0 g
  2. stirringstirred for 24 hours at room temperature
  3. customThe resulting mixture is evaporated in vacuo to dryness
  4. dissolutionthe residue dissolved in 1500 ml
  5. extractionThis solution is extracted twice with sodium carbonate solution
  6. washwashed neutral with water
  7. customdried
  8. customevaporated in vacuo to dryness
  9. customThe residue is twice crystallized from methylene chloride/ diethyl ether

Sources & evidence

ORD record
ord-30a1ebd7a36c4a12bf55ca42d0e8de85
Source dataset
uspto-grants-1977_10
Patent number
US04053600

Reaction notes

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