Chlorosulfonyl isocyanate → HCID 54229696, compound

HRID 1109297Notes

Reaction equation

HRID 1109297 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[CH2:13][O:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].ClS([N:27]=[C:28]=[O:29])(=O)=O.C(O)(=O)C.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:28]([N:11]1[C:10](=[O:14])[C:9](=[CH:8][C:7]2[CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]([OH:18])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[CH2:13][O:12]1)(=[O:29])[NH2:27]

Participants

6

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 21899381Acetic acid--water (1/1)HCID 53742514HCID 53742514, compound

Product 1

HCID 54229696HCID 54229696, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 212 mg (0.7 mmol) of the thus obtained 4-(3,5di-tert-butyl-4-hydroxybenzylidene)isoxazolidin-3-one in toluene (6 ml) was added 67 μl (0.77 mmol) of chlorosulfonyl isocyanate while being stirred with heating at 100° C. and allowed to react for 10 minutes. The reaction mixture was evaporated to give a residue, which was added with 4 ml of a acetic acid/water (2/1) mixture and stirred with heating at 100° C. for 10 minutes. The reaction mixture was evaporated to give a residue, which was dissolved in ethyl acetate. The reaction mixture was washed with water and saturated brine and evaporated under reduced pressure to give a residue, which was chromatographed on silica gel (n-hexane/ethyl acetate=2/1) to give 127 mg of the objective compound (Ie-1) in 52% yield. A part of product was recrystallized from a dichloromethane/n-hexane mixture.

Workup

  1. customto react for 10 minutes
  2. customThe reaction mixture was evaporated
  3. customto give a residue, which
  4. stirringstirred
  5. temperaturewith heating at 100° C. for 10 minutes
  6. customThe reaction mixture was evaporated
  7. customto give a residue, which
  8. washThe reaction mixture was washed with water and saturated brine
  9. customevaporated under reduced pressure
  10. customto give a residue, which
  11. customwas chromatographed on silica gel (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-be9c8495953c4e319e67302bd0fb514d
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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