Acetic Acid → 3,7-Dichloro-1,2,4-benzotriazine

HRID 1834022Notes

Reaction equation

HRID 1834022 reaction equation
[Cl:1][C:2]1[N:3]=[N+:4]([O-])[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.[Cl-].[NH4+].C(O)(=O)C>O.[Zn]>[Cl:1][C:2]1[N:3]=[N:4][C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 130939893,7-Dichloro-1-oxo-1lambda~5~,2,4-benzotriazine

Product 1

HCID 205554783,7-Dichloro-1,2,4-benzotriazine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A suspension of 21,8 g (0.1 mole) of 3,7-dichlorobenzo-1,2,4-triazine 1-oxide, 7.5 g of zinc dust and 5.5 g of ammonium chloride in 400 ml of water was stirred vigorously at room temperature for 24 hours. 50 ml of glacial acetic acid were then added, the mixture was stirred for a further hour and the insoluble constituents were then filtered off. The latter were extracted twice with methylene chloride. The combined methylene chloride solutions were washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was recrystallized from wash benzine. 7.5 g, that is to say 37% of theory, of 3,7-dichloro-benzo-1,2,4-triazine with a melting point of 113°-115° C were obtained. ##STR36## (Preparation according to process variant (a))

Workup

  1. stirringthe mixture was stirred for a further hour
  2. filtrationthe insoluble constituents were then filtered off
  3. extractionThe latter were extracted twice with methylene chloride
  4. washThe combined methylene chloride solutions were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized
  8. washfrom wash benzine

Sources & evidence

ORD record
ord-bafbf11dfefe4b6b83c049bf0034251e
Source dataset
uspto-grants-1978_01
Patent number
US04067981

Reaction notes

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