Chloride → HCID 14257507, compound

HRID 1030003Notes

Reaction equation

HRID 1030003 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:5]=[CH:4][CH:3]=1.[Cl-].N1C=CC=CC=1.[C:23](Cl)(Cl)=[O:24]>ClCCCl>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([S:12]([N:15]=[C:23]=[O:24])(=[O:13])=[O:14])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 1049PyridineHCID 6371Phosgene2×HCID 14257494HCID 14257494, compound

Product 1

HCID 14257507HCID 14257507, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

100 g of methyl 6-chloro-2-aminosulfonyl-benzoate were suspended in 300 ml of 1,2-dichloroethane, 123 g of thionuyl chloride were added with stirring, and the mixture was slowly heated to the reflux temperature. After it had been stirred for 5 hours under reflux, it was cooled to 55° C., 1.5 ml of pyridine were added and the mixture again heated to the reflux temperature, while introducing phosgene. After 4 hours' treatment with phosgene gas, the reaction mixture was concentrated under reduced pressure and flushed with nitrogen. The oil which remained (105 g) was used, without further purification, for the subsequent stages.

Workup

  1. temperaturethe mixture was slowly heated to the reflux temperature
  2. stirringAfter it had been stirred for 5 hours
  3. temperatureunder reflux
  4. temperaturethe mixture again heated to the reflux temperature
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customflushed with nitrogen
  7. customwas used, without further purification, for the subsequent stages

Sources & evidence

ORD record
ord-bbb5d67d6bc44daca68c8b83ce345a04
Source dataset
uspto-grants-1992_04
Patent number
US05104441

Reaction notes

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