Chlorosulfonyl isocyanate → HCID 54370431, compound

HRID 1109364Notes

Reaction equation

HRID 1109364 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[CH:8]=[C:9]1[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]1=[O:16])([CH3:4])([CH3:3])[CH3:2].ClS([N:29]=[C:30]=[O:31])(=O)=O.C(O)(=O)C.O>C1(C)C=CC=CC=1>[C:30]([N:11]1[C:12]([CH3:14])([CH3:15])[CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:19]([OH:20])=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]=2)[C:10]1=[O:16])(=[O:31])[NH2:29]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 21899381Acetic acid--water (1/1)HCID 54442207HCID 54442207, compound

Product 1

HCID 54370431HCID 54370431, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 329 mg (1 mmol) of the thus obtained 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-5,5-dimethylpyrrolidin-2-one in 2 ml of dry toluene was added 96 μl (1.1 mmol) of chlorosulfonyl isocyanate under a nitrogen atmosphere. The reaction mixture was heated at 90° C. for 10 minutes and evaporated to give a residue, which was added with 2.4 ml of acetic acid/water (2/1) and heated at 90° C. for 10 minutes. The reaction mixture was then poured into ice-water and extracted with dichloromethane three times. The organic layers were collected and washed with water, dried over magnesium sulfate and then evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=1/1) and recrystallized from ether to give 107 mg of the objective compound (Id-1) in 29% yield.

Workup

  1. customevaporated
  2. customto give a residue, which
  3. temperatureheated at 90° C. for 10 minutes
  4. extractionextracted with dichloromethane three times
  5. customThe organic layers were collected
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give a residue, which
  10. customwas chromatographed on silica gel (toluene/ethyl acetate=1/1)
  11. customrecrystallized from ether

Sources & evidence

ORD record
ord-cdfeb5ed3458404f9d57cc63d2fab109
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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