4-Chloro-1,2-diaminobenzene → 5-Chloro-2,1,3-benzoselenadiazole

HRID 1094130Notes

Reaction equation

HRID 1094130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[Se:10](=O)=O>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][Se:10][N:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 72634-Chloro-1,2-diaminobenzeneHCID 24007Selenium Dioxide

Product 1

HCID 4135755-Chloro-2,1,3-benzoselenadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chlorobenzene-1,2-diamine (1.50 g, 10.5 mmol) in EtOH (15 mL) was heated to reflux and selenium dioxide (1.28 g, 11.5 mmol) was added. The reaction was refluxed for 30 min and cooled to ambient temperature. The precipitated solid was filtered, washed thoroughly with H2O and dried under high vacuum to give the title compound. MS: m/z=219 (M+1).

Workup

  1. temperatureto reflux
  2. temperatureThe reaction was refluxed for 30 min
  3. filtrationThe precipitated solid was filtered
  4. washwashed thoroughly with H2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-64f0822c934a410a971df6c830efa65c
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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