Nitric Acid → 5-Chloro-4-nitro-2,1,3-benzoselenadiazole

HRID 1968751Notes

Reaction equation

HRID 1968751 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]([CH:14]=1)=[N:11][Se:12][N:13]=2>S(=O)(=O)(O)O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]([C:14]=1[N+:1]([O-:4])=[O:2])=[N:11][Se:12][N:13]=2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4135755-Chloro-2,1,3-benzoselenadiazole

Product 1

HCID 43662215-Chloro-4-nitro-2,1,3-benzoselenadiazoleYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At 0-5° C., a 65% aqueous solution of HNO3 (6.5 g, 103.5 mmol, 3.3 equiv) was added to a solution of 5-chloro-benzo[1,2,5]selenadiazole (6.82 g, 31.35 mmol; 1H NMR (400 MHz, d6-DMSO): δ=7.96 (d, J=1.4 Hz, 1H), 7.82 (d, J=10.2 Hz, 1H), 7.52 (dd, J=10.2/1.4 Hz, 1H)) in sulfuric acid (95-97%, 100 ml). After 2 hours at 5° C., the reaction mixture was poured onto ice water, and the precipitate was filtered off. The solid was washed with water and dried under high vacuum to afford the title compound (8.14 g, 99%). 1H NMR (400 MHz, d6-DMSO): δ=8.13 (d, J=8.5 Hz, 1H), 7.82 (d, J=8.5 Hz, 1H).

Workup

  1. additionthe reaction mixture was poured onto ice water
  2. filtrationthe precipitate was filtered off
  3. washThe solid was washed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-daf5b3ca408941168145382a1181cb16
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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