Chlorosulfonyl isocyanate → HCID 54379467, compound

HRID 1109291Notes

Reaction equation

HRID 1109291 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[O:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].ClS([N:27]=[C:28]=[O:29])(=O)=O>C1(C)C=CC=CC=1>[C:28]([N:11]1[C:10](=[O:14])[C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[O:13][CH2:12]1)(=[O:29])[NH2:27]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 54151026HCID 54151026, compound

Product 1

HCID 54379467HCID 54379467, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)oxazolidin-4-one (100 mg, 0.33 mmole) suspended in dried toluene (0.5 ml), 32 μl of chlorosulfonyl isocyanate (0.363 mmole) was added under nitrogen atmosphere with stirring and the mixture was dissolved for 2 min. After the solution colored to brown, it was heated at 90° C. for 10 min. and toluene was evaporated under reduced pressure. A mixed solution (0.8 ml) of acetic acid and water (2:1) was added thereto, and the mixture was heated at 90° C. under nitrogen atmosphere for 10 min. The resulting mixture was poured into ice-water, which was subjected to extraction with dichloromethane, then the organic layer was washed with water, dried over sodium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=1:1), and recrystallized from ether-n-hexane, whereby 73 mg of the objective compound was obtained in 64% yield. The physical constants are described on Table 1.

Workup

  1. dissolutionthe mixture was dissolved for 2 min
  2. customtoluene was evaporated under reduced pressure
  3. additionA mixed solution (0.8 ml) of acetic acid and water (2:1) was added
  4. temperaturethe mixture was heated at 90° C. under nitrogen atmosphere for 10 min
  5. additionThe resulting mixture was poured into ice-water, which
  6. extractionwas subjected to extraction with dichloromethane
  7. washthe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe obtained residue was separated
  11. customrecrystallized from ether-n-hexane

Sources & evidence

ORD record
ord-851594bf8d57453486ac2d57da48b252
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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