Phenol → HCID 54105243, compound

HRID 327699Notes

Reaction equation

HRID 327699 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([NH:10][S:11](Cl)(=[O:13])=[O:12])[CH3:9].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([O:7][S:11](=[O:13])(=[O:12])[NH:10][CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 516892Sodium BicarbonateHCID 11040810Ethylsulfamoyl chloride

Product 1

HCID 54105243HCID 54105243, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 18.8 g (0.2 mole) of phenol and 38.4 g (0.27 mole) of ethylaminosulfonyl chloride (Preparation 25) in 150 ml of toluene was stirred and heated at reflux for 16 hr. The solution was cooled and then treated with 250 ml of a 20% sodium bicarbonate solution. The layers were separated and the organic layer was washed successively with 250 ml of a 20% sodium bicarbonate solution, two 300-ml portions of water and dried (magnesium sulfate). The solvent was evaporated under reduced pressure and the oily residue was purified by chromatography (4.5×105 cm glass column; 550 g of silica gel; ethyl acetate-hexanes, 1:16). Fractions containing the product were combined and the solvents evaporated under reduced pressure to give 28.5 g (71%) of the title compound as a colorless liquid. Elemental analysis suggested that the product contained water.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. temperatureThe solution was cooled
  4. customThe layers were separated
  5. washthe organic layer was washed successively with 250 ml of a 20% sodium bicarbonate solution, two 300-ml portions of water
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was evaporated under reduced pressure
  8. customthe oily residue was purified by chromatography (4.5×105 cm glass column; 550 g of silica gel; ethyl acetate-hexanes, 1:16)
  9. additionFractions containing the product
  10. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a446f5e497048b698a545120a87df79
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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