Hydrochloric Acid → 3,4-bis-(3-Fluorophenyl)-1,2,5-thiadiazole-1,1-dioxide

HRID 18711

Reaction equation

HRID 18711 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=O)=O)[CH:6]=[CH:7][CH:8]=1.[S:20]([NH2:24])([NH2:23])(=[O:22])=[O:21]>CO>[F:2][C:3]1[CH:4]=[C:5]([C:9]2[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:24][S:20](=[O:22])(=[O:21])[N:23]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82267SulfamideHCID 225742141,2-Bis(3-fluorophenyl)ethane-1,2-dione

Product 1

HCID 685709543,4-bis-(3-Fluorophenyl)-1,2,5-thiadiazole-1,1-dioxideYield 72.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
66 °C

Procedure

Hydrogen chloride is bubbled through a solution of 3,3′-difluorobenzil (20) (3.81 g, 15.7 mmol) and sulfamide (1.53 g, 15.9 mmol) in methanol (15 mL) for 0.5 min followed by heating at 66° C. for 2 h. The reaction mixture is cooled to RT, the solvent rotary evaporated, and the residue triturated from heptane to give 3.50 g of the product 21.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. customthe solvent rotary evaporated, and the residue triturated from heptane

Sources & evidence

ORD record
ord-534affd4eb524b5fbc80708d57bf766a
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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