Furfurylamine → N-(Furan-2-ylmethyl)tetrahydrofuran-3-sulfonamide

HRID 1776224Notes

Reaction equation

HRID 1776224 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[CH2:12][CH2:11][CH:10]([S:13](Cl)(=[O:15])=[O:14])[CH2:9]1>N1C=CC=CC=1>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][NH:7][S:13]([CH:10]1[CH2:11][CH2:12][O:8][CH2:9]1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 49762850Oxolane-3-sulfonyl chloride

Product 1

HCID 86702150N-(Furan-2-ylmethyl)tetrahydrofuran-3-sulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of furfurylamine (0.171 g, 1.8 mmol) in pyridine (2 mL) at 0° C. was slowly added tetrahydrofuran-3-sulfonyl chloride (0.250 g, 1.5 mmol). The reaction mixture was warmed to room temperature and stirred for 16 hrs. The mixture was concentrated and the residue was dissolved in ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the product (0.220 g, 65%) as a thick oil. 1H NMR (300 MHz, CDCl3) δ 7.41 (s, 1H), 6.36 (dd, 1H, J=3.3, 2.1 Hz), 6.31 (d, 1H, J=3.3 Hz), 4.68 (t, 1H, J=5.4 Hz), 4.36 (d, 2H, J=6.0 Hz), 4.05 (dd, 1H, J=10.2, 5.7 Hz), 4.02-3.78 (m, 3H), 3.65 (m, 1H), 2.36-2.10 (m, 2H).

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9ddda6eab19440aaacebf22ae8c3284f
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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