Guaiacol → HCID 54046715, compound

HRID 1613436Notes

Reaction equation

HRID 1613436 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[CH3:10][NH:11][S:12](Cl)(=[O:14])=[O:13]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][S:12](=[O:14])(=[O:13])[NH:11][CH3:10]

Participants

4

Reactant 2

HCID 460GuaiacolHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 54046715HCID 54046715, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 12.4 g (0.1 mole) of 2-methoxyphenol (guaiacol; Aldrich) and 13.1 g (0.1 mole) of methylsulfamoyl chloride (Preparation 22) in 150 ml of toluene was stirred and treated at reflux for 2 hr. The solvent was evaporated under reduced pressure and the only residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A, PrepPAK® 500A silica, ethyl acetate-hexanes, 1:2; flow rate 150 ml/min). Fractions containing the product were combined and the solvents evaporated under reduced pressure to yield an oil that solidified upon standing. The solid was recrystallized from benzene-petroleum-ether (30°-60° C.) to give 14.3 g (66%) of the title compound as a white solid, mp 68°-71° C.

Workup

  1. additiontreated
  2. temperatureat reflux for 2 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe only residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A, PrepPAK® 500A silica, ethyl acetate-hexanes, 1:2; flow rate 150 ml/min)
  5. additionFractions containing the product
  6. customthe solvents evaporated under reduced pressure
  7. customto yield an oil that
  8. customThe solid was recrystallized from benzene-petroleum-ether (30°-60° C.)

Sources & evidence

ORD record
ord-242073e560fb4322a958bea2988aa3d5
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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