Carbon Dioxide → HCID 44459222, compound

HRID 1613805Notes

Reaction equation

HRID 1613805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[S:10]([N:13]=C=O)(=[O:12])=[O:11].O.C(=O)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([O:8][S:10](=[O:12])(=[O:11])[NH2:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 97433-FluorophenolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 44459222HCID 44459222, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled (ice bath) solution of 11.2 g (0.1 mole) of 3-fluorophenol (98%, Aldrich) in 75 ml of toluene was added 9.1 ml (14.8 g, 0.105 mol) of chlorosulfonyl isocyanate, and the solution heated at reflux overnight. The solution was cooled and cautiously treated dropwise with water until carbon dioxide evolution ceased. An oil separated and ethyl acetate was added to dissolve this oil. The layers were separated and the organic layer was washed with water, dried (sodium sulfate) and concentrated to give an oil which gradually crystallized. The solid was purified by column chromatography on 400 g of silica gel eluted with methylene chloride. The appropriate fractions were combined and concentrated to yield 9.2 g (48%) of the title compound which was recrystallized from benzene to give a white solid, mp 53°-55° C.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux overnight
  3. temperatureThe solution was cooled
  4. customAn oil separated
  5. additionethyl acetate was added
  6. dissolutionto dissolve this oil
  7. customThe layers were separated
  8. washthe organic layer was washed with water
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated
  11. customto give an oil which
  12. customgradually crystallized
  13. customThe solid was purified by column chromatography on 400 g of silica gel
  14. washeluted with methylene chloride
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-35d9613f82cc4a12bc54cdc7c9d70878
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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