Furfurylamine → HCID 10512356, compound

HRID 1776221Notes

Reaction equation

HRID 1776221 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH:9]([S:11](Cl)(=[O:13])=[O:12])[CH3:10]>N1C=CC=CC=1>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][NH:7][S:11]([CH:9]([CH3:10])[CH3:8])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 824082-Propanesulfonyl chloride

Product 1

HCID 10512356HCID 10512356, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of furfurylamine (1.040 g, 10.7 mmol) in pyridine (10 mL) at 0° C. was slowly added 2-propanesulfonyl chloride (1.0 mL, 8.9 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 (0.84 g, 46%) as a yellowish thick oil. 1H NMR (300 MHz, CDCl3) δ 7.40 (dd, 1H, J=1.8, 0.9 Hz), 6.35 (dd, 1H, J=3.3, 1.8 Hz), 6.29 (d, 1H, J=3.3 Hz), 4.42 (br s, 1H), 4.33 (d, 2H, J=5.7 Hz), 3.08 (m, 1H), 1.35 (d, 6H, J=6.9 Hz).

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-335adb6648c041cdaeddba1e1020d0c7
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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