3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine → N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}-2-(furfurylsulfinyl)acetamide

HRID 704911Notes

Reaction equation

HRID 704911 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][CH2:11][CH2:12][NH2:13].[CH2:17]([S:23]([CH2:25][C:26](OC1C=CC([N+]([O-])=O)=CC=1)=[O:27])=[O:24])[C:18]1[O:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:26](=[O:27])[CH2:25][S:23]([CH2:17][C:18]1[O:22][CH:21]=[CH:20][CH:19]=1)=[O:24]

Participants

4

Reactant 2

HCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamineHCID 14514722p-Nitrophenyl 2-(furfurylsulfinyl)acetate

Product 1

HCID 14514723N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}-2-(furfurylsulfinyl)acetamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamine (16.3 g) was dissolved in 400 ml of methylene chloride, and p-nitrophenyl 2-(furfurylsulfinyl)acetate (22.58 g) was added little by little. The mixture was stirred at room temperature for 18 hours. The organic layer was washed successively with a 1N aqueous NaOH solution and water and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 21.29 g (yield 74%) of N-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl}-2-(furfurylsulfinyl)acetamide.

Workup

  1. washThe organic layer was washed successively with a 1N aqueous NaOH solution and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-25c2360036b7470894f48b8245b57c5b
Source dataset
uspto-grants-1991_01
Patent number
US04988828

Reaction notes

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