Hydrochloric Acid → 3-Amino-1,2,4-benzotriazine-1-oxide

HRID 341788Notes

Reaction equation

HRID 341788 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=[O:2].[N:11]#[C:12][NH2:13].Cl.[OH-].[Na+]>C(O)(=O)C>[N+:1]1([O-:2])[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:12]([NH2:13])[N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 9864CyanamideHCID 14798Sodium Hydroxide

Product 1

HCID 794703-Amino-1,2,4-benzotriazine-1-oxideYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 10 g 2-nitroaniline and 20 g cyanamide is heated for 5 min to 100° C., cooled, mixed with 25 ml conc. hydrochloric acid and carefully heated to 70° C. After subsidence of the vigorous reaction, one cools to room temp., adds dropwise thereto 50 ml semiconce. caustic soda lye, heats for 30 min to 100° C., cools, filters and washes the precipitate with hot glacial acetic acid. There remain 9.1 g of title compound (78% of theory) of the m.p. 272°-274° C.

Workup

  1. temperatureis heated for 5 min to 100° C.
  2. temperaturecooled
  3. customAfter subsidence of the vigorous reaction, one cools to room temp.
  4. additionadds dropwise

Sources & evidence

ORD record
ord-6afef906f78f490a9201b00e9d00908a
Source dataset
uspto-grants-1999_01
Patent number
US05856325

Reaction notes

Loading…