Thionyl Chloride → HCID 10546147, compound

HRID 609883Notes

Reaction equation

HRID 609883 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:14]2[N:18]([CH2:19][CH2:20][CH2:21]O)[C:17](=[O:23])[CH2:16][S:15]2)[CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[OH:10])([CH3:3])[CH3:2].S(Cl)([Cl:26])=O>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:14]2[N:18]([CH2:19][CH2:20][CH2:21][Cl:26])[C:17](=[O:23])[CH2:16][S:15]2)[CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[OH:10])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10497178HCID 10497178, compound

Product 1

HCID 10546147HCID 10546147, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (50 ml) solution of the 2-(3,5-diisopropyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one (1.97 g) obtained in Reference Example 1 was added thionyl chloride (1.04 g) under a nitrogen atmosphere, then the mixture was refluxed for 1 hour. The solvent was evaporated under reduced pressure, and to the residue were added brine and chloroform. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; dichloromethane) to afford 1.25 g (60%) of the title compound as pale yellow crystals. mp 105-106° C. NMR (CDCl3, 60 MHz) δ: 1.23 (12H, d, J=6.6 Hz), 1.5-2.1 (2H, m), 2.6-3.8 (6H, m), 3.67 (2H, brs), 5.20 (1H, s), 5.50 (1H, brs), 6.88 (2H, s)

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. additionto the residue were added brine and chloroform
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; dichloromethane)

Sources & evidence

ORD record
ord-fad2c1129ba94f8e8b5f19fd9e564822
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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