Dimethylformamide → Saccharin

HRID 1438879Notes

Reaction equation

HRID 1438879 reaction equation
[K].[S:2]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])(O)(=[O:4])=[O:3].C[N:16](C)C=O.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[S:2]1(=[O:4])(=[O:3])[C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](=[O:9])[NH:16]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6371PhosgeneHCID 124382-Sulfobenzoic acidHCID 5462222Potassium

Product 1

HCID 5143Saccharin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a four necked flask equipped with a stirrer, a thermometer, a condenser and a phosgene inlet, were charged 24.0 g (0.1 mole) of the monopotassium salt of o-sulfobenzoic acid ##STR10## 150 ml of toluene and 0.22 g (0.003 mole) of dimethylformamide. The mixture was stirred at 80° C and 23 g of phosgene were introduced into the mixture over 4 hours. The reaction was continued by maintaining the temperature at 80° - 90° C under refluxing with stirring for 3 hours. After the reaction, nitrogen gas was injected into the mixture to remove excess phosgene. The reaction mixture was filtered to remove potassium chloride and the filtrate was condensed and a colorless condensate was obtained.

Workup

  1. customInto a four necked flask equipped with a stirrer
  2. temperatureby maintaining the temperature at 80° - 90° C
  3. temperatureunder refluxing
  4. stirringwith stirring for 3 hours
  5. customAfter the reaction, nitrogen gas
  6. customto remove excess phosgene
  7. filtrationThe reaction mixture was filtered
  8. customto remove potassium chloride
  9. customcondensed
  10. customa colorless condensate was obtained

Sources & evidence

ORD record
ord-41a7ad950bf748cd940b3c1afe022d6e
Source dataset
uspto-grants-1977_11
Patent number
US04057555

Reaction notes

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