Guanidine Hydrochloride → 3-Amino-1,2,4-benzotriazine

HRID 1247622Notes

Reaction equation

HRID 1247622 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC([O-])(C)C.[K+].[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-])=O>CS(C)=O>[NH2:4][C:3]1[N:5]=[N:12][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:2]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 7416NitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 883363-Amino-1,2,4-benzotriazineYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring mixture of guanidine hydrochloride (160 mg, 1.7 mmol) and t-BuOK (670 mg, 6 mmol) in DMSO (4 mL) was added one portion of nitrobenzene (123 mg, 1 mmol) at room temperature. The mixture turned red in one minute. In 20 to 30 minutes the mixture was quenched with a saturated, aqueous solution of ammonium chloride. A yellow precipitate was formed and removed by filtration. The precipitate was then washed with water, dried in the air, and recrystallized from benzene or ethanol to give 105 mg (72%) of 3-amino-1,2,4-benzotriazine. The melting point was determined to be 203–205° C., consistent with the melting point (207° C.) of 3-amino-1,2,4-benzotriazine synthesized by other known methods (J. Chem. Soc. (B) (1970) 911).

Workup

  1. customIn 20 to 30 minutes the mixture was quenched with a saturated, aqueous solution of ammonium chloride
  2. customA yellow precipitate was formed
  3. customremoved by filtration
  4. washThe precipitate was then washed with water
  5. customdried in the air
  6. customrecrystallized from benzene or ethanol

Sources & evidence

ORD record
ord-ee9818244242460289efada25e1f7a5e
Source dataset
uspto-grants-2006_10
Patent number
US07129349B2

Reaction notes

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