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N-(Phenylthio)phthalimide

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N-(Phenylthio)phthalimide Basic information
Product Name:N-(Phenylthio)phthalimide
Synonyms:N-(Phenylthio)phthalimide;2-(Phenylthio)-1,3-isoindolinedione;N-(Phenylthio)phthalimide>;1H-Isoindole-1,3(2H)-dione, 2-(phenylthio)-;2-(Phenylthio)-1H-isoindole-1,3(2H)-dione;2-(Phenylthio)-1H-isoindol-1,3(2H)-dione;2-(Phenylthio)isoindoline-1,3-dione;N-(Phenylthio)phthalimide
CAS:14204-27-4
MF:C14H9NO2S
MW:255.29
EINECS:
Product Categories:N-Substituted Phthalimides;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Others;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;N-Substituted Maleimides, Succinimides & Phthalimides
Mol File:14204-27-4.mol
N-(Phenylthio)phthalimide Structure
N-(Phenylthio)phthalimide Chemical Properties
Melting point 160-163 °C(lit.)
Boiling point 432.2±28.0 °C(Predicted)
density 1.42±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility DMSO: soluble25mg/mL, clear, yellow
pka-3.05±0.20(Predicted)
form powder to crystal
color White to Light yellow
CAS DataBase Reference14204-27-4
Safety Information
Safety Statements 24/25
WGK Germany 3
HS Code 29309090
MSDS Information
ProviderLanguage
SigmaAldrich English
N-(Phenylthio)phthalimide Usage And Synthesis
UsesUsed as a mild sulfenylating reagent.
PreparationN-(Phenylthio)phthalimide is prepared by reaction of Benzenesulfenyl Chloride with Phthalimide in the presence of Triethylamine.
Preparation(a) Preparation of benzenesulfenyl chloride. To a stirred solution of 55 gm (0.5 mole) of benzene thiol in 300 ml of η -pentane at 0°C is added chlorine gas until an assay (GC) of the resulting red-orange solution shows quantitative conversion to the sulfenyl chloride. The reaction usually re­quires about 39 gm (0.6 mole) of chlorine.
(b) Reaction of benzenesulfenyl chloride with phthalimide. To a stirred solution of 73.5 gm (0.5 mole) of phthalimide in 200 ml of dimethylforma-mide is first added 60 gm (0.6 mole) of triethylamine. Then the sulfenyl chloride solution from (a) is slowly added dropwise. The reaction mixture is stirred for \ hr, poured into 2 liters of cold water, filtered, and dried to afford 121 gm (95%), m.p. 160-161°C (recrystallized from ethanol).
Complex imides such as camphorimide and 9,10-dihydroanthracene-9,10-endo-a,/3-succinimide have been alkylated in methylene dichloride with alkyl halides, using tetrabutylammonium bromide as a phase-transfer catalyst and aqueous potassium hydroxide as a base.
Preparation of N-(Phenylthio)phthalimide
N-(Phenylthio)phthalimide Preparation Products And Raw materials
Preparation Products1H-Isoindol-1-one, 3-hydroxy--->N-tert-Butylbenzenesulfenamide-->Ethyl 4-phenylsulfanylbenzoate
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