Acetic Acid → n-(acetylsulfamoyl)acetamide

HRID 2296367Notes

Reaction equation

HRID 2296367 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[S:5]([N:11]=C=O)([N:8]=[C:9]=[O:10])(=[O:7])=[O:6].[CH:14]1C=CC=CC=1>>[C:9]([NH:8][S:5]([NH:11][C:1](=[O:4])[CH3:2])(=[O:7])=[O:6])(=[O:10])[CH3:14]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 241BenzeneHCID 77898Sulphonyl diisocyanate

Product 1

HCID 253729n-(acetylsulfamoyl)acetamide

Conditions

Temperature
60 °C

Procedure

12 g of anhydrous acetic acid are dissolved in 150 ml of absolute benzene and 14.8 g of sulfuryl diisocyanate (prepared in accordance with German Pat. No. 940,351) are added dropwise within 20 minutes at ambient temperature, accompanied by stirring. The temperature rises from 21° to 39° C. and CO2 evolution as well as a precipitation of a colorless precipitate occur. The reaction mixture is heated by means of an oil bath to 60° C. accompanied by stirring until the evolution of the gas is at an end, which takes 2 hours. The reaction mixture is cooled, the precipitate removed by suction filtering and dried at 60° C. 17.8 g of colorless crystals are obtained (98.8% of theory), m.p. 167°-169° C. (decomp.) which can be recrystallized from isopropanol and acetic acid.

Workup

  1. addition940,351) are added dropwise within 20 minutes at ambient temperature
  2. customrises from 21° to 39° C.
  3. customCO2 evolution as well as a precipitation of a colorless precipitate
  4. stirringby stirring until the evolution of the gas
  5. temperatureThe reaction mixture is cooled
  6. customthe precipitate removed by suction
  7. filtrationfiltering
  8. customdried at 60° C

Sources & evidence

ORD record
ord-b8f7482279534da287f0cdc17d30aa03
Source dataset
uspto-grants-1984_01
Patent number
US04429063

Reaction notes

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