ERYSOLIN synthesis

8synthesis methods

Product Name:ERYSOLIN
CAS Number:504-84-7
Molecular formula:C6H11NO2S2
Molecular Weight:193.29

4478-93-7 Synthesis

4478-93-7
284 suppliers
$30.00/1mg

504-84-7
24 suppliers
$295.00/50mg

Yield:504-84-7 66%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at -20 - 20; for 3 h;Inert atmosphere;

Steps:

15 Oxidation of Sulforaphane

EXAMPLE 15
Oxidation of Sulforaphane
1.77 g of sulforaphane (1 equivalent) obtained in Example 4, as well as 15 mL of dichloromethane are introduced into the reactor, and the mixture is then degassed and set under nitrogen.
1.6 equivalents of meta-chloroperbenzoic acid solubilized in 25 mL of dichloromethane are placed in an isobaric dropping funnel and poured dropwise (within 20 mins) at room temperature, into the reactor.
The addition causes exothermy for producing oxidized sulforaphane i.e. 1-isothiocyanato-4-(methylsulfonyl)butane or 4-methylsulfonylbutyl-isothiocyanate,
Stirring is maintained for 2 hours at room temperature.
A white precipitate forms.
After this period, the reactor is cooled to -20° C. and maintained for 1 hour at this temperature before carrying out filtration.
The filtrate and the solid are analyzed by NMR.
The solid contains derivatives of MCPBA, while the filtrate contains the oxidized product, as well as a few traces of aromatic residues and of residual sulforaphane.
The product is washed with a minimum of a solution saturated with NaHCO₃ in order to remove the benzoic acid, and then chromatographed on silica gel, eluent CH₂Cl₂ 100% and then AcOEtT 100%.
After evaporation of the solvents, 1.27 g of a yellowish liquid which solidifies are obtained with a yield of 66%.
TLC: Eluent: AcOEt 100%;
Developer: phosphomolybdic acid;[0261] Rf=0.5. [0262] ¹H NMR (300 MHz; CDCl₃): [0263] δ (ppm): 3.61 (t, 2H, -CH₂-NCS); 3.07 (t, 2H, -S(O)₂-CH₂); 2.94 (s, 3H, CH₃-S(O)₂-); 2.07-1.85 (m, 4H, -CH₂-CH₂-). [0264] ¹³C NMR (75 MHz; CDCl₃): [0265] δ (ppm): 53.63; 44.44; 40.74; 28.55; 19.79. [0266] UV spectrum: [0267] λ_max=245 nm [0268] Melting point: 58° C.