N-ethylcarbamate → 7,9-dichloro-2-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one

HRID 986499Notes

Reaction equation

HRID 986499 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[C:10]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][N:11]=1.C(N[C:24](=O)[O-:25])C>O>[Cl:8][C:7]1[C:2]2[NH:1][C:24](=[O:25])[N:11]3[N:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=[C:10]3[C:3]=2[CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

4

Reactant 2

HCID 22042200N-ethylcarbamateHCID 178507830HCID 178507830, compound

Product 1

HCID 1357362467,9-dichloro-2-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(2-amino-3,5-dichlorophenyl)-5-phenyl-1H-1,2,4-triazole (6 g) and ethylcarbamate (50 g) is heated under nitrogen at 195° for 6 hours after which it is cooled to 80°, poured into water (1000 ml) and stirred 16 hours. The product is collected, washed with water, then methanol (300 ml) and air dried. The crude material is recrystallized from 12:1 2-methoxyethanol-water to afford pure 7,9-dichloro-2-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one, mp 309°-311°.

Workup

  1. temperatureis heated under nitrogen at 195° for 6 hours after which it
  2. temperatureis cooled to 80°
  3. customThe product is collected
  4. washwashed with water
  5. dry with materialmethanol (300 ml) and air dried
  6. customThe crude material is recrystallized from 12:1 2-methoxyethanol-water

Sources & evidence

ORD record
ord-86238c241b0f4081971063d1a7c7383b
Source dataset
uspto-grants-1987_12
Patent number
US04713383

Reaction notes

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