Sodium Hydroxide → 4-Chloro-3-nitro-1,2-benzenediamine

HRID 505237Notes

Reaction equation

HRID 505237 reaction equation
I.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([C:11]=1[N+:12]([O-:14])=[O:13])=[N:8][Se][N:10]=2.OS([O-])=O.[Na+].[OH-].[Na+]>Cl>[Cl:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[C:7]([NH2:8])[C:6]([NH2:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 43662215-Chloro-4-nitro-2,1,3-benzoselenadiazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 37368244-Chloro-3-nitro-1,2-benzenediamineYield 86%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

At room temperature, an aqueous solution of hydroiodic acid (48%, 25 ml) was added to a solution of 5-chloro-4-nitro-benzo[1,2,5]selenadiazole (8.14 g, 31.01 mmol) in concentrated aqueous hydrochloric acid (76 ml). After 2 hours at room temperature, a 5% aqueous solution of NaHSO3 (150 ml) was added, and the mixture was stirred for 15 minutes. At 0° C., concentrated aqueous NaOH solution was added until the pH value reached 8. The mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (4.98 g, 86%), which was used in the next transformation without further purification. 1H NMR (400 MHz, d6-acetone): δ=6.81 (d, J=7.7 Hz, 1H), 6.68 (d, J=7.7 Hz, 1H), 5.12 (br s, 2H), 4.78 (br s, 2H). MS (ES−): 186.2 (M−H)−.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09acaa1fb0f44d79a326cdfbc3a90a29
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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