Chlorosulfonyl isocyanate → 3,5-Bis(1-methylethyl)-4-(sulfamoyloxy)benzoic acid methyl ester

HRID 2289677Notes

Reaction equation

HRID 2289677 reaction equation
C(=O)=[N:2][S:3](Cl)(=[O:5])=[O:4].[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:20])=[C:13]([CH:21]([CH3:23])[CH3:22])[CH:12]=1>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:12]=[C:13]([CH:21]([CH3:22])[CH3:23])[C:14]([O:20][S:3](=[O:4])(=[O:5])[NH2:2])=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:16]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 12133075HCID 12133075, compound

Product 1

HCID 541866693,5-Bis(1-methylethyl)-4-(sulfamoyloxy)benzoic acid methyl esterYield 49.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Chlorosulfonyl isocyanate (2.12 mL, 24.3 mmol) was added slowly to a warm solution of 3,5-diisopropyl-4-hydroxy-benzoic acid methyl ester (5.47 g, 23.1 mmol) in 300 mL toluene. The resulting solution was heated to reflux for 6 hours and then cooled to room temperature and concentrated to give a brown oil. Quenched with 200 g ice and extracted with ethyl acetate. The organic solution was dried over magnesium sulfate, filtered, and concentrated to give a tan solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 3.58 g of the title compound as an off-white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 6 hours
  3. concentrationconcentrated
  4. customto give a brown oil
  5. customQuenched with 200 g ice
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a tan solid

Sources & evidence

ORD record
ord-2c813653e699413ea3518baf09e824fb
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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