1-Propanethiol, 3-(triethoxysilyl)- → Phthalimide

HRID 2087095Notes

Reaction equation

HRID 2087095 reaction equation
C1([N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=S)CCCCC1.SCCC[Si](OCC)(OCC)[O:23]CC>C(Cl)(Cl)Cl>[C:8]1(=[O:23])[NH:7][C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]12

Participants

4

Reactant 2

HCID 846581-Propanethiol, 3-(triethoxysilyl)-HCID 570830882-Cyclohexyl-3-sulfanylideneisoindol-1-one

Product 1

HCID 6809PhthalimideYield 119.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A 1-quart (0.946l) glass reactor was charged with 400 ml of chloroform, 55.4 g (0.21 mole) of N-cyclohexylthiophthalimide, and 47.6 g (0.20 mole) of 3-mercaptopropyltriethoxysilane dissolved in 400 ml of chloroform. The reaction was stirred and allowed to stand overnight to give white needles of phthalimide (35.2 g) which were separated by filtration and identified by mass spectrometry analysis. The solvent was distilled from the filtrate to give 56.9 g of an oil identified as cyclohexyl-3-dithiopropyltriethoxysilane by mass spectrometry analysis. This oil (53 g) was dissolved in 100 ml of acetone and homogeneously dispersed into N330 carbon black, with the acetone being stripped away.

Sources & evidence

ORD record
ord-9d47d995142342c1b543f152ed53f71d
Source dataset
uspto-grants-2004_04
Patent number
US06727374B2

Reaction notes

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