Hydrochloric Acid → 3-(Pyridin-3-yl)-4-phenyl-1,2,5-thiadiazole-1,1-dioxide Hydrochloride

HRID 2053629

Reaction equation

HRID 2053629 reaction equation
[ClH:1].[C:2]1([C:8](=O)[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18]([NH2:22])([NH2:21])(=[O:20])=[O:19]>CO>[ClH:1].[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:22][S:18](=[O:20])(=[O:19])[N:21]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82267SulfamideHCID 109875561-Phenyl-2-(pyridin-3-yl)ethan-1,2-dione

Product 1

HCID 685697783-(Pyridin-3-yl)-4-phenyl-1,2,5-thiadiazole-1,1-dioxide Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Hydrogen chloride gas is bubbled into a solution of 1-phenyl-2-(pyridin-3-yl)ethan-1,2-dione (1.63 g, 7.7 mmol, J. Org. Chem., 1999, 64, 6102) and sulfamide (750 mg, 7.7 mmol) in methanol (10 mL) until the solution begins to reflux. The gas flow is turned off, and the solution stirred at 65° C. for 3 h then cooled to rt. The solid that formed is filtered and dried to give 2.06 g of the product 497. MS: m/z 272 (M++1).

Workup

  1. temperatureto reflux
  2. temperaturethen cooled to rt
  3. customThe solid that formed
  4. filtrationis filtered
  5. customdried

Sources & evidence

ORD record
ord-865c7bf6da804114910cc1932dd4b093
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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