Chlorosulfonyl isocyanate → HCID 54381889, compound

HRID 1109290Notes

Reaction equation

HRID 1109290 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[S: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)[S:13][CH2:12]1)(=[O:29])[NH2:27]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 1300035-(3,5-Bis(tert-butyl)-4-hydroxyphenyl)methylene-4-thiazolidinone

Product 1

HCID 54381889HCID 54381889, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

5-(3,5-Di-tert-butyl-4-hydroxybenzylidene)thiazolidin-4-one (479 mg, 1.5 mmole) described in Kokai 62-42977 was suspended in dried toluene (3 ml), to which chlorosulfonyl isocyanate (144 μl;1.65 mmole) was added with stirring under nitrogen atmosphere, to obtain a transparent solution of orange color. Furthermore, the solution was heated at 90° C. for 10 min., from which toluene was evaporated under reduced pressure, then 3.6 ml of mixed solution of acetic acid and water (2:1) was added thereto. The resulting mixture was heated at 90° C. for 10 min. and poured into ice-water, which was subjected to extraction with dichloromethane. The obtained organic layer was washed with water and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (chloroform:acetone=20:1), whereby 377 mg of the objective compound was obtained, which was recrystallized from ethanol-ether in 53% yield. The physical constants are described on Table 1.

Workup

  1. additionwas added
  2. customto obtain a transparent solution of orange color
  3. customwas evaporated under reduced pressure
  4. addition3.6 ml of mixed solution of acetic acid and water (2:1) was added
  5. additionpoured into ice-water, which
  6. extractionwas subjected to extraction with dichloromethane
  7. washThe obtained organic layer was washed with water and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe obtained residue was separated

Sources & evidence

ORD record
ord-53341ae822a442ccb8fda710e2eb2137
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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