Guaiacol → HCID 53763908, compound

HRID 1494051Notes

Reaction equation

HRID 1494051 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].C(N(C(C)C)CC)(C)C.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][S:21](=[O:23])(=[O:22])[N:20]([CH3:25])[CH3:19]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 53763908HCID 53763908, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 24.8 g (0.2 mole) of guaiacol (Aldrich) and 34.9 g (0.27 mole) of diisopropylethylamine (Hunig's base, Aldrich) in 200 ml of toluene was added to a solution of 29 ml (0.27 mole) of dimethylsulfamoyl chloride (Aldrich) in 75 ml of toluene and the stirred reaction mixture was heated at reflux for 12 hr. The reaction mixture was successively washed with four 300 ml portions of 6N hydrochloric acid solution, 400 ml of water, three 200 ml portions of 20% sodium hydroxide solution, 400 ml of water and dried (magnesium sulfate). The solvent was evaporated under reduced pressure to give a brown, viscous oil that solidified upon standing. The solid was recrystallized from ethyl ether-petroleum ether and was collected by filtration. The filtrate was evaporated under reduced pressure and the viscous, brown oil was purified by chromatography (4.5×90 cm glass column, 5.30 g of silica gel, ethyl acetate-hexanes, 1:8). Fractions containing the desired compound were combined and the solvents evaporated under reduced pressure to yield 2.5 g (5%) of the title compound as a light yellow liquid.

Workup

  1. customthe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 12 hr
  4. washThe reaction mixture was successively washed with four 300 ml portions of 6N hydrochloric acid solution, 400 ml of water, three 200 ml portions of 20% sodium hydroxide solution, 400 ml of water
  5. dry with materialdried (magnesium sulfate)
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a brown, viscous oil that
  8. customThe solid was recrystallized from ethyl ether-petroleum ether
  9. filtrationwas collected by filtration
  10. customThe filtrate was evaporated under reduced pressure
  11. customthe viscous, brown oil was purified by chromatography (4.5×90 cm glass column, 5.30 g of silica gel, ethyl acetate-hexanes, 1:8)
  12. additionFractions containing the desired compound
  13. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-4aaa6422c2cd4f068bfc9274b7e16373
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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