Hydrochloric Acid → 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

HRID 722942Notes

Reaction equation

HRID 722942 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].O.Cl>COCCOCCOC>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][S:9]1(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7243O-PhenylenediamineHCID 82267Sulfamide

Product 1

HCID 153721H,3H-2,1,3-Benzothiadiazole 2,2-dioxideYield 45.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of orthophenylenediamine (20 g) and sulfamide (20.4 g) in diglyme (200 ml) was stirred at 160° C. for 2 hours, the reaction mixture was cooled to room temperature, water (200 g) was poured thereto, hydrochloric acid was added until pH 1, extracted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (14.2 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (13.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 1N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e680f9d95bc249b3b64c37d2742340e2
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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