Triethylamine → 4-benzyl-2-(1-Phenylthiomethyl)isothiazolidin-3-one 1,1-dioxide

HRID 1078634Notes

Reaction equation

HRID 1078634 reaction equation
[C:1]1([CH2:7][CH:8]([C:14]([O:16]CC)=O)[CH2:9][S:10](Cl)(=[O:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([S:25][CH2:26]Cl)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([N:30](CC)CC)C>C(#N)C>[CH2:7]([CH:8]1[CH2:9][S:10](=[O:11])(=[O:12])[N:30]([CH2:26][S:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]1=[O:16])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81623Chloromethyl phenyl sulphideHCID 21475177Ethyl 2-benzyl-3-chlorosulphonylpropionate

Product 1

HCID 194282414-benzyl-2-(1-Phenylthiomethyl)isothiazolidin-3-one 1,1-dioxideYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-benzylisothiazolidin-3-one 1,1-dioxide 4 (0.9 g; 4 mmol), chloromethyl phenyl sulfide (0.63 g; 4 mmol) and triethylamine (0.40 g; 4 mmol) in dry acetonitrile (10 mL) was refluxed for 2 h. The solvent was removed in vacuo and the residue was dissolved in methylene chloride and extracted with water (50 mL) 5% hydrochloric acid (50 mL) and 5% sodium bicarbonate (50 mL). The organic layer was dried and evaporated, leaving a crude product (0.8 g) which was purified by flash chromatography (silica gel/hexane:methylene chloride), yielding 0.32 g of 4-benzyl-2-(1-Phenylthiomethyl)isothiazolidin-3-one 1,1-dioxide. This was oxidized to compound 10 by stirring overnight with m-chloroperbenzoic acid (2.2 eq) in methylene chloride. Compound 10 was obtained by evaporating off the solvent, adding ether and collecting the precipitated product, mp 137°-8° C. (0.38 g; 90% yield). 1H NMR: δ 2.85(m, 1H), 3.3(m,2H), 3.5(m,2H), 4.87(s,2H), 7.15(dd,2H), 74.0-7.25(m,3H), 7.81-7.70(m,3H), 8.0(m,2H).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. extractionextracted with water (50 mL) 5% hydrochloric acid (50 mL) and 5% sodium bicarbonate (50 mL)
  5. customThe organic layer was dried
  6. customevaporated
  7. customleaving a crude product (0.8 g) which
  8. customwas purified by flash chromatography (silica gel/hexane:methylene chloride)

Sources & evidence

ORD record
ord-5fe0274649da40cc8145476ea5b2599f
Source dataset
uspto-grants-1996_08
Patent number
US05550139

Reaction notes

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