N,N-Dimethylaniline → 5-Chloro-8,9-dimethoxy-1,2,4-triazolo-[1,5-c]-quinazoline

HRID 972718Notes

Reaction equation

HRID 972718 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[C:11]([CH:12]=1)=[N:10][C:9](=O)[N:8]1[NH:14][CH:15]=[N:16][C:7]=21.O(Cl)[Cl:20].CN(C)C1C=CC=CC=1>>[Cl:20][C:9]1[N:8]2[N:14]=[CH:15][N:16]=[C:7]2[C:6]2[CH:5]=[C:4]([O:17][CH3:18])[C:3]([O:2][CH3:1])=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24646Chlorine monoxideHCID 178486881HCID 178486881, compound

Product 1

HCID 214051295-Chloro-8,9-dimethoxy-1,2,4-triazolo-[1,5-c]-quinazoline

Procedure

300 mg of 8,9-Dimethoxy-1,2,4-triazolo-[1,5-c]quinazoline-5-one is refluxed with 5 ml Phospherous oxychloride and a catalytic amount of N,N-dimethylamline for 18 hours. The reaction mixture is then evaporated in vacuo to dryness; the residue taken up in methylene chloride and the methylene chloride layer extracted several times with cold sodium bicarbonate solution, with water, dried and then avaporated in vacuo to dryness. The residue is crystallized from methylene chloride/diethyl ether to give 5-chloro-8,9-dimethoxy-1,2,4-triazolo-[1,5-c]-quinazoline, m.p. 258°-260°.

Workup

  1. customThe reaction mixture is then evaporated in vacuo to dryness
  2. extractionthe methylene chloride layer extracted several times with cold sodium bicarbonate solution
  3. dry with materialwith water, dried
  4. customThe residue is crystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-5bf5a50e666f40e9b5932fbbb202dab8
Source dataset
uspto-grants-1977_10
Patent number
US04053600

Reaction notes

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