Synthesis of bis(2-aminoethyl)sulfide

Preparation of bis(2-aminoethyl)sulfide

Forty-three grams (1.0 mole) of ethyleneimine 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 beta-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 beta-aminoethyl mercaptan sublimes during the first part of the distillation. Bis-2-aminoethyl sulfide is collected at 130-1310/22 m. There is obtained 29.8 g., or a 50% yield.

Reference: J. Am. Chem. Soc, 63, 2363 (1941).





InChI Key


Canonical SMILES


MeSH Synonyms

lanthionamine, lanthionamine hydrobromide, lanthionamine hydrochloride

Depositor-Supplied Synonyms

2,2′-Thiobis(ethylamine), 871-76-1, Lanthionamine, 2,2′-Thiobisethylamine, 3-Thiacadaverine, Bis(2-aminoethyl) sulfide, Ethanamine, 2,2′-thiobis-, 2,2′-thiodiethanamine, Monoethanolamine sulfide, 2,2′-Thiodiethylamine, 2-(2-aminoethylsulfanyl)ethanamine, 1,7-Diaza-4-thiaheptane, 1,5-Diamino-3-thiapentane, 2,2′-sulfanediyldiethanamine, 2,2′-Thiobis[ethylamine], 2-[(2-AMINOETHYL)SULFANYL]ETHANAMINE, Bis(beta-aminoethyl)sulfide, Ethylamine, 2,2′-thiobis-, C4H12N2S, beta,beta’-Diaminodiethyl sulfide, EINECS 212-810-3, 2-Aminoethyl Sulfide, NSC 203144, aminoethylthioethylamine, ACMC-209qic, Ethanamine,2′-thiobis-, Ethylamine,2′-thiobis-, AC1L2DCE, 2,2-Thiobis(ethylamine), Bis-(2-aminoethyl)sulfide, AC1Q7E8N, bis-(beta-aminoethyl)sulfide, SCHEMBL50767, 2,2′-Diaminodiethyl Sulfide, Bis(.beta.-aminoethyl)sulfide, DTXSID6061232, CTK8B2524, JONTXEXBTWSUKE-UHFFFAOYSA-, JONTXEXBTWSUKE-UHFFFAOYSA-N, MolPort-001-986-749, ZINC1737510, ANW-38626, AR-1J3015, MFCD00039783, NSC203144, 2-[(2-aminoethyl)sulfanyl]ethylamine, 2-(2-Amino-ethylsulfanyl)-ethylamine, AKOS000670614, .beta.,.beta.’-Diaminodiethyl sulfide, FCH2581150, NSC-203144, RTR-032038, AK307732, AN-47838, BAS 02988465, BBV-32653687, K553, LP058880, OR012328, KB-163919, TL8005657, FT-0633042, C-36788, I14-19926, InChI=1/C4H12N2S/c5-1-3-7-4-2-6/h1-6H2

Removed Synonyms

3-Thia-1,5-pentanediamine, C4-H12-N2-S, CID70096, T1538, 93407-17-1

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