Sulfuric Acid → HCID 86680560, compound

HRID 1487381Notes

Reaction equation

HRID 1487381 reaction equation
P(Cl)(Cl)(Cl)=O.S(=O)(=O)(O)O.[Cl:11][C:12]1[N:20]=[CH:19][C:18]([S:21](=[O:32])(=[O:31])[NH:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)=[CH:17][C:13]=1[C:14]([NH2:16])=O>>[Cl:11][C:12]1[N:20]=[CH:19][C:18]([S:21]([NH:22][C:23]2[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=2)(=[O:32])=[O:31])=[CH:17][C:13]=1[C:14]#[N:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24813Phosphorus oxychlorideHCID 86680558HCID 86680558, compound

Product 1

HCID 86680560HCID 86680560, compoundYield 72.6%

Conditions

Temperature
90 °C

Procedure

3.4 ml (36.2 mmol) of phosphoryl chloride and a drop of concentrated sulfuric acid are added to 0.315 g (0.906 mmol) of 2-chloro-5-(N-(3,5-difluorophenyl) sulfamoyl)nicotinamide. The reaction mixture is stirred for 2 hours at 90° C. and then added drop by drop to ice. The brown solid is filtered, rinsed with water and then dried under vacuum. 0.217 g of 6-chloro-5-cyano-N-(3,5-difluorophenyl)pyridine-3-sulfonamide is obtained in the form of a light brown solid (yield=72%).

Workup

  1. additionadded drop by drop to ice
  2. filtrationThe brown solid is filtered
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3f772e6b459c4c9b8edb4fe3ec4d524a
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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