Carbon Dioxide → HCID 54463613, compound

HRID 1613778Notes

Reaction equation

HRID 1613778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[S:11]([N:14]=C=O)(=[O:13])=[O:12].O.C(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][S:11](=[O:13])(=[O:12])[NH2:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 72583,4-DichlorophenolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 54463613HCID 54463613, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 16.3 g (0.1 mole) of 3,4-dichlorophenol in 100 ml of toluene was heated at reflux utilizing a Dean-Stark trap to remove any water that may have been present. The solution was cooled in an ice bath, treated with 9.1 ml (14.8 g, 0.105 mole) of chlorosulfonyl isocyanate, and heated at reflux overnight. The solution was cooled in an ice bath, vigorously stirred, and treated dropwise with water until carbon dioxide evolution ceased. The solid which precipitated was collected by filtration, washed with water and benzene, dried, and recrystallized from benzene to yield 19.9 g (82%) of a white solid, mp 121°-123° C.

Workup

  1. temperatureat reflux
  2. customto remove any water that
  3. temperatureThe solution was cooled in an ice bath
  4. temperatureheated
  5. temperatureat reflux overnight
  6. temperatureThe solution was cooled in an ice bath
  7. customThe solid which precipitated
  8. filtrationwas collected by filtration
  9. washwashed with water and benzene
  10. customdried
  11. customrecrystallized from benzene

Sources & evidence

ORD record
ord-61b8116c2a504b419d64ca2af4c2ad23
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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