Sulfamide → 1-(3,4-Difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818835Notes

Reaction equation

HRID 1818835 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[S:17](N)(N)(=[O:19])=[O:18]>COCCOCCOC>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:16][S:17]2(=[O:19])=[O:18])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 29067155N-(3,4-difluorophenyl)benzene-1,2-diamine

Product 1

HCID 468333821-(3,4-Difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 47%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

Dry diglyme (10 mL) was added to a flask equipped with a dropping funnel under a nitrogen atmosphere and brought to a vigorous reflux. N-(3,4-difluorophenyl)benzene-1,2-diamine (1.03 g, 4.7 mmol) and sulfamide (0.54 g, 5.6 mmol) were dissolved in 5 mL of diglyme and placed in the dropping funnel. The mixture was added dropwise to the flask over 15 minutes and then refluxing was continued for an additional 15 minutes. The mixture was cooled to ambient temperature and the reaction mixture was evaporated using high temperature. The crude reaction product was purified by flash chromatography (SiO2, 3-50% ethyl acetate/hexane) to provide 1-(3,4-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.62 g, 47%) as a pink solid:

Workup

  1. customequipped with a dropping funnel under a nitrogen atmosphere
  2. additionThe mixture was added dropwise to the flask over 15 minutes
  3. temperaturerefluxing
  4. customthe reaction mixture was evaporated
  5. customThe crude reaction product
  6. customwas purified by flash chromatography (SiO2, 3-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cbd4c2aa79c24966add16131ce207654
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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