Hydrochloric Acid → 5-(2-Amino-4,5-dimethoxyphenyl)-s-triazole

HRID 329186Notes

Reaction equation

HRID 329186 reaction equation
ClC1[N:11]2[CH:12]=[N:13][N:14]=[C:10]2[C:9]2[CH:8]=[C:7]([O:15][CH3:16])[C:6]([O:17][CH3:18])=[CH:5][C:4]=2[N:3]=1.[OH-].[K+].Cl>>[NH2:3][C:4]1[CH:5]=[C:6]([O:17][CH3:18])[C:7]([O:15][CH3:16])=[CH:8][C:9]=1[C:10]1[NH:14][N:13]=[CH:12][N:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 214051435-Chloro-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline

Product 1

HCID 214390785-(2-Amino-4,5-dimethoxyphenyl)-s-triazole

Procedure

To a flask containing 46 gms. of 5-chloro-8,9-dimethoxy-1,2,4,triazolo[4,3-c]quinazoline is added 1000 ml. of a 10% KOH solution and the resulting mixture heated to reflux. A gentle reflux is maintained overnight after which time the mixture is neutralized to pH 7.0 with cooling and stirring by adding dropwise a 1:1 HCl solution and the resulting precipitate filtered off. The aqueous layer is washed 3 or 4 times with ethyl acetate, dried and evaporated in vacuo to dryness. The residue is recrystallized from ethanol to obtain 5-(2-amino-4,5-dimethoxyphenyl)-s-triazole, m.p. 205°-210° C.

Workup

  1. additionTo a flask containing 46 gms
  2. temperatureA gentle reflux
  3. temperatureis maintained overnight after which time the mixture
  4. temperaturewith cooling
  5. filtrationthe resulting precipitate filtered off
  6. washThe aqueous layer is washed 3 or 4 times with ethyl acetate
  7. customdried
  8. customevaporated in vacuo to dryness
  9. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-93212d3c44ca4d218547048c5bb6b0fd
Source dataset
uspto-grants-1977_04
Patent number
US04020083

Reaction notes

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