1-Decanethiol → bis-(2-decylsulfanyl-ethyl)-amine

HRID 1988301Notes

Reaction equation

[OH-].[Na+].[CH2:3]([SH:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.Cl[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]Cl>C(O)C>[CH2:3]([S:13][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][S:13][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaOH (3 g, 75 mmol) and decanethiol (15.5 ml, 75 mmol) in ethanol (75 ml) was added to a solution of bis(2-chloroethyl)amine hydrochloride (4.4 g, 25 mmol) in ethanol (50 ml) at 0° C. The solution was stirred for 2 hours at 0° C. and then for another 16 h at room temperature. After filtering, the filtrate was evaporated to dryness. The residue was taken up with dry ether and filtered again. After evaporation of the solvent under vacuum, the product remained as a colourless semi-solid. Yield: 9.4 g (90%). 1H-NMR (CDCl3) δ 0.87 (6H, t, CH3), 1.25-1.4 (28H, m, SC2H4C7H14CH3), 1.56 (4H, qn, SCH2CH2C8H17), 1.88 (1H, s, NH), 2.52 (4H, qt, SHCH2C9H19), 2.69 (4H, t, SCH2CH2NH), 2.82 (4H, t, NCH2).

Workup

waitfor another 16 h at room temperature
filtrationAfter filtering
customthe filtrate was evaporated to dryness
filtrationfiltered again
customAfter evaporation of the solvent under vacuum

Sources & evidence

ORD record: ord-1c34b3edc58b448abf67c5cd1b7988a7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07554001B2

Reaction notes

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