O-Phenylenediamine → 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

HRID 1348677Notes

Reaction equation

HRID 1348677 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[S:9](N)(N)(=[O:11])=[O:10]>COCCOCCOC>[NH:7]1[S:9](=[O:11])(=[O:10])[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=2

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 82267Sulfamide

Product 1

HCID 153721H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of 1,2-phenylenediamine (91 mg, 0.84 mmol) and sulfamide (81 mg, 0.84 mmol) in diglyme (2.5 ml) is stirred at 155° C. for 1.5 h. After cooling to RT, the reaction solution is poured into ice-water (15 ml) and the product is extracted with ethyl acetate. The solvent is distilled off under reduced pressure and the red residue is purified by flash chromatography (1:1 ethyl acetate/toluene).

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. distillationThe solvent is distilled off under reduced pressure
  3. customthe red residue is purified by flash chromatography (1:1 ethyl acetate/toluene)

Sources & evidence

ORD record
ord-0fedbf911bae4a9a9095dd6a03873a76
Source dataset
uspto-grants-2007_05
Patent number
US07211592B2

Reaction notes

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