2-Nitroaniline → Benzofuroxan

HRID 2052432Notes

Reaction equation

HRID 2052432 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[OH-].[K+].Cl[O-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[N+:1]1([O-:3])[O:2][N:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=12

Participants

6

Reactant 3

HCID 69462-NitroanilineHCID 14797Potassium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 68075Benzofuroxan

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

18.4 kg (133 moles) of 2-nitroaniline and 0.42 kg (1.3 moles) of tetrabutylammonium bromide are dissolved in 70 kg of toluene. After the addition of 25.3 kg (226 moles) of 50% aqueous potassium hydroxide solution, there is added at 15° to 20° C., during one hour, 110 kg (185 moles) of an aqueous sodium hypochlorite solution. After the addition has been completed, the reaction mixture is allowed to react at 15° to 20° C. for 3 hours, and the aqueous phase is then separated. There is obtained in this manner a solution of benzofurazan-1-oxide in toluene, which solution is suitable for use directly for further reactions, for example for reaction with an acetoacetic acid derivative to the corresponding quinoxaline-1,4-dioxide.

Workup

  1. additionis added at 15° to 20° C., during one hour
  2. additionAfter the addition
  3. customto react at 15° to 20° C. for 3 hours
  4. customthe aqueous phase is then separated

Sources & evidence

ORD record
ord-582b497de3304ffe904bca3dba4f8bfa
Source dataset
uspto-grants-1980_01
Patent number
US04185018

Reaction notes

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