Pyridine → HCID 19693798, compound

HRID 2399590Notes

Reaction equation

HRID 2399590 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13]([O:15][CH3:16])=[O:14])[CH3:12])=[CH:7][C:6]=1[S:17]([NH2:20])(=[O:19])=[O:18])=[O:4].S(Cl)(Cl)=O.N1C=CC=CC=1.[C:31](Cl)(Cl)=[O:32]>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13]([O:15][CH3:16])=[O:14])[CH3:12])=[CH:7][C:6]=1[S:17]([N:20]=[C:31]=[O:32])(=[O:19])=[O:18])=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 24386Thionyl ChlorideHCID 19693802HCID 19693802, compound

Product 1

HCID 19693798HCID 19693798, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5.0 g of 2-methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonamide are suspended in 17 ml of 1,2-dichloroethane. 4 ml of thionyl chloride are added and the reaction mixture is heated at boiling for 5 h. The reaction mixture is cooled to room temperature, 0.3 ml of pyridine is added, phosgene is passed into the reaction mixture, and the solution is heated at reflux for 4 h. The reaction mixture is concentrated to give 6.3 g of an oil which is employed directly in the subsequent reaction (Examples m, n, o).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperaturethe solution is heated
  3. temperatureat reflux for 4 h
  4. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-77dd300a08d94b8ea2df798adbbcac39
Source dataset
uspto-grants-1995_09
Patent number
US05449812

Reaction notes

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