2- Aminoethyl sulfide

Reaction with Sulfur Nucleophiles, Because sulfai is highly nucleophilic, reactions of aziridines with sulfur nucleophiles generally proceed rapidly (111) and with good yields. The reaction of hydrogen sulfide [7783-06S-J with ethyleneimine yields cysteamine [60-23-1] (2-mercaptoethylamine) or bis(2-aminoethyl)sulfide [871-76-1] (2,112) depending on the molar ratio of the reactants. The use of NaHS for the synthesis of cysteamine has also been described (113). 

Forty-three grams (1.0 mole) of ethyleneimine (p. 153) (Caution— volatile and toxic substance) is placed in a flask equipped with a reflux condenser. The reaction mixture is held at 60° by external cooling while a stream of hydrogen sulfide is introduced. After there is no evolution of heat upon introduction of hydrogen sulfide (about 50 minutes), the liquid, viscous reaction mixture is dissolved in 1.25 times its volume of absolute ethanol and cooled overnight in the refrigerator. The precipitated /S-aminoethyl mercaptan (5.6 g.) is filtered off, and the ethanol is evaporated from the filtrate under reduced pressure. The residual liquid is distilled under reduced pressure, and 4.9 g. additional /ff-aminoethyl mercaptan sublimes during the first part of the distillation. Bis-2-aminoethyl sulfide is collected at 130-131 °/22 m. There is obtained 29.8 g., or a 50% yield. 

Several specialized silica-based functionalized platinum scavengers such as N-acetyl-L-cysteine, 2-aminoethyl sulfide, 2-mercaptoethyl ethyl sulfide, 3-mercapto-propyl ethyl sulfide, pentaerythritol 2-mercaptoacetate ethyl sulfide and triamine ethyl sulfide amide, developed by Strem Chemicals, are also available. These scavengers are highly stable and available in pure forms, which successfully scavenge platinum metal ions in batch processes. 

Oxidation of phenyl 2-aminoethyl sulfide by dopamine P-hydroxylase from bovine adrenals in the presence of ascorbate as the electron donor resulted in the formation of phenyl 2-aminoethyl sulfoxide. The product was probably of the S-configura-tion[171. 

The reaction of the anhydrides 60 with bis(2-aminoethyl) sulfide gave the sulfides 182, which were converted by the action of carbonic ester into compounds 183 [106, 107],... 

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