Ethanolamine → 3-((2-Hydroxyethyl)amino)tetrahydrothiophene 1,1-dioxide

HRID 85712Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[S:12]1(=[O:18])(=[O:17])[CH:16]=[CH:15][CH2:14][CH2:13]1>C(O)C>[OH:4][CH2:3][CH2:2][NH:1][CH:14]1[CH2:15][CH2:16][S:12](=[O:18])(=[O:17])[CH2:13]1

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of 2-aminoethanol (310 mg, 5.08 mmol), triethylamine (514 mg, 5.08 mmol) and 2,3-dihydrothiophene 1,1-dioxide (200 mg, 1.693 mmol) in ethanol (3 mL) was heated up at 78° C. for 16 hours. TLC indicated the starting material was consumed and desired product was formed (30% methanol/ethyl acetate). The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel chromatography with 0-35% methanol/ethyl acetate to provide the title compound as a colorless oil (260 mg, 86%). 1H NMR (400 MHz, CHLOROFORM-d) δ 3.78-3.56 (m, 3H), 3.38-3.21 (m, 2H), 3.14-3.00 (m, 1H), 2.94 (dd, J=13.3, 6.0 Hz, 1H), 2.85-2.68 (m, 2H), 2.53-2.34 (m, 1H), 2.22-2.03 (m, 1H).

Workup

customwas consumed

Sources & evidence

ORD record: ord-13f51c145ffb4e21be9c0353f06a8ebf
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

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