ChemicalBook CAS DataBase List Cyclohexylthiophthalimide

Cyclohexylthiophthalimide synthesis

5synthesis methods

Product Name:Cyclohexylthiophthalimide
CAS Number:17796-82-6
Molecular formula:C14H15NO2S
Molecular Weight:261.34

2439-85-2 Synthesis

2439-85-2
148 suppliers
$15.00/5g

2550-40-5
124 suppliers
$14.00/25mL

17796-82-6
250 suppliers
$5.00/10g

Yield:17796-82-6 52%

Reaction Conditions:

in acetonitrile at 100; under 750.075 Torr; for 0.166667 h;Microwave irradiation;

Steps:

1
Example 1: Synthesis of 2-(Cyclohexylthio)isoindoline-l,3-dione.; The following compound was used as an intermediate product in the synthesis of sulfenyl guanidine prodrugs of metformin.Dicyclohexyl disulphide (0.51 g, 2.21 mmol) and iV-bromophthalimide (0.50 g, 2.21 mmol) in anhydrous ACN (20 ml) were irradiated at 100 ⁰C (1 bar) in a microwave reactor for 10 min. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography eluting with hexane/ethyl acetate (2:1) solution to obtain the compound 1 as a light yellow solid (0.29 g, 52%).¹H NMR (CDCl₃): δ 7.95-7.91 (2H, dd, ³J_HH = 5.46 Hz, ⁴J_HH = 3.07 Hz), 7.81-7.76 (2H, dd, ³JHH = 5.46 Hz, ⁴J_HH = 3.07 Hz), 3.22-3.15 (IH, tt, ³J_HH = 3.63, 10.88 Hz), 1.95-1.88 (2H, m), 1.84-1.75 (2H, m), 1.65-1.57 (IH, m), 1.43-1.33 (2H, m), 1.32-1.18 (3H, m).

References:

UNIVERSITY OF EASTERN FINLAND;HUTTUNEN, Kristiina;LEPPÄNEN, Jukka;RAUTIO, Jarkko;VEPSÄLÄINEN, Jouko WO2010/100337, 2010, A1 Location in patent:Page/Page column 6-7

FullText