Ethylamine → N-Ethyltetrahydro-3-furanmethanamine

HRID 1647842Notes

Reaction equation

HRID 1647842 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1)(=O)=O.[CH2:18]([NH2:20])[CH3:19].[OH-].[Na+]>>[O:8]1[CH2:9][CH2:10][CH:6]([CH2:5][NH:20][CH2:18][CH3:19])[CH2:7]1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 14798Sodium HydroxideHCID 15335290Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

Product 1

HCID 22355252N-Ethyltetrahydro-3-furanmethanamine

Conditions

Temperature
75 °C

Procedure

A mixture comprising 4.09g of (tetrahydro-3 -furanyl)methyl tosylate, 17 ml of 70% aqueous ethylamine solution and 8.2 ml of 2 N aqueous sodium hydroxide solution was stirred at 75° C. for 6 hours. The reaction fluid was concentrated under a reduced pressure to obtain crude N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine. To this were added 2.00 g of 1,1-bis(methylthio)-2-nitroethylene and 20 ml of acetonitrile. The resulting mixture was refluxed for 3 hours. The reaction fluid was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2) to obtain 0.81 g of 1-[N-{(tetrahydro-3-furanyl)methyl}-N-ethylamino]-1-methylthio-2-nitroethylene.

Workup

  1. concentrationThe reaction fluid was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-6802d20c344f461e9e4b731e4b81cacb
Source dataset
uspto-grants-1995_07
Patent number
US05434181

Reaction notes

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