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

2550-40-5

17796-82-6

Example 1: Synthesis of 2-(cyclohexylthio)isoindoline-1,3-dione 1,2-Dicyclohexyl disulfide (0.51 g, 2.21 mmol) was dissolved in anhydrous acetonitrile (20 mL) with N-bromophthalimide (0.50 g, 2.21 mmol) in a microwave reactor. The microwave irradiation reaction was carried out at 100 °C and 1 bar pressure for 10 min. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by fast column chromatography with the eluent of hexane/ethyl acetate (2:1, v/v) to afford the target compound 2-(cyclohexylsulfanyl)isoindoline-1,3-dione as a light yellow solid (0.29 g, 52% yield). 1H NMR (CDCl3) δ: 7.95-7.91 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 7.81-7.76 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 3.22-3.15 (1H, tt, 3JHH = 3.63 Hz, 10.88 Hz), 1.95-1.88 (2H, m), 1.84-1.75 (2H, m), 1.65-1.57 (1H, m), 1.43-1.33 (2H, m), 1.32-1.18 (3H, m).

2439-85-2 Synthesis

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

2550-40-5
129 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

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