Sulfuric Acid → HCID 178526297, compound

HRID 341791Notes

Reaction equation

HRID 341791 reaction equation
[N+:1]1([O-:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3](N)[N:2]=1.S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+].CCOCC>O>[N+:1]1([O-:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]([OH:14])[N:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 794703-Amino-1,2,4-benzotriazine-1-oxideHCID 23668193Sodium Nitrite

Product 1

HCID 178526297HCID 178526297, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 7.5 g (46 mmol) 1,2,4-benzotriazine-3-amine 1-oxide (Chem. Ber. 46, 3522 (1913) in 75 ml water and 27 ml conc. sulphuric acid one adds dropwise at room temp. a solution of 13.3 g sodium nitrite in 25 ml water. One leaves to stand overnight, filters, takes up in soda solution, washes with ether, acidifies the aqueous phase, filters and recrystallises from glacial acetic acid. One isolates 4.7 g of title compound (63% of theory) of the m.p. 238-239° C.

Workup

  1. customOne leaves
  2. customrecrystallises from glacial acetic acid

Sources & evidence

ORD record
ord-e00ca9f02f4b4c2d9b2a7c3f4db76525
Source dataset
uspto-grants-1999_01
Patent number
US05856325

Reaction notes

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