Chlorosulfonyl isocyanate → HCID 18698846, compound

HRID 2289676Notes

Reaction equation

HRID 2289676 reaction equation
C(=O)=[N:2][S:3](Cl)(=[O:5])=[O:4].[CH:8]([C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([CH:20]([CH3:22])[CH3:21])[C:18]=1[OH:19])[CH:14]=[O:15])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[S:3](=[O:4])(=[O:5])([O:19][C:18]1[C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][C:11]=1[CH:8]([CH3:10])[CH3:9])[NH2:2]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehyde

Product 1

HCID 18698846HCID 18698846, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Chlorosulfonyl isocyanate (21.6 mL, 248 mmol) was added slowly to a warm solution of 3,5-diisopropyl-4-hydroxy-benzaldehyde (24.4 g, 118 mmol) in 500 mL toluene. The resulting solution was heated to reflux for 4 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 11.15 g of the title compound as an off-white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 4 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-d35d0df4bb1e4d2bb516043786455cf2
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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