Pyridine → HCID 23358655, compound

HRID 232527Notes

Reaction equation

HRID 232527 reaction equation
S(Cl)(Cl)=O.[CH2:5]([S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH2:19])(=[O:18])=[O:17])(=[O:9])=[O:8])[CH3:6].N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27]>ClCCCl>[CH2:5]([S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([N:19]=[C:26]=[O:27])(=[O:17])=[O:18])(=[O:9])=[O:8])[CH3:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 24386Thionyl ChlorideHCID 23358662HCID 23358662, compound

Product 1

HCID 23358655HCID 23358655, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

102.8 g (0.865 mol) of thionyl chloride were added to 71.8 g (0.288 mol) of 2-(ethylsulfonyl)benzenesulfonamide in 500 ml of 1,2-dichloroethane in the course of 30 minutes while stirring at from 70° to 80° C., and the refluxed mixture was stirred for 2.5 hours. After the mixture had been cooled to 50° C., 2 ml of pyridine were added and gaseous phosgene was passed into the refluxed mixture in the course of 5 hours while stirring. Evaporating down gave 84.1 g of the title compound, which was taken up directly in 1,2-dichloroethane for storage.

Workup

  1. stirringthe refluxed mixture was stirred for 2.5 hours
  2. customwas passed into the refluxed mixture in the course of 5 hours
  3. stirringwhile stirring
  4. customEvaporating down

Sources & evidence

ORD record
ord-487e8eb5ae034fa093c8ab1ec69f93e0
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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