HCID 14228262, compound → 2,1,3-Benzoxadiazole, 4,6-dichloro-, 1-oxide

HRID 580649Notes

Reaction equation

HRID 580649 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[N:12]=[N+]=[N-]>C(O)(=O)C>[CH:5]1[C:4]2[C:3](=[N:12][O:10][N+:9]=2[O-:11])[C:2]([Cl:1])=[CH:7][C:6]=1[Cl:8]

Participants

3

Reactant 1

HCID 14228262HCID 14228262, compound

Product 1

HCID 36237742,1,3-Benzoxadiazole, 4,6-dichloro-, 1-oxideYield 92.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.63 g (2.7 mmol) of 2,4-dichloro-6-nitroazidobenzene and 25 ml glacial acetic acid is made and is refluxed for three to six hours. This is then poured over ice water, filtered and washed with water to yield 0.51 g (92.1% yield) of 4,6-dichlorobenzofuroxan, having a melting point of 105 to 105.5° C. Experimental runs result in yields ranging from 75 to 92%. The material can be recrystallized from ethanol/water if desired.

Workup

  1. temperatureis refluxed for three to six hours
  2. filtrationfiltered
  3. washwashed with water

Sources & evidence

ORD record
ord-99ed9a02a76742a2b9043ed7524586ad
Source dataset
uspto-grants-1988_06
Patent number
US04754040

Reaction notes

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