2-(Methylamino)ethanol → N-(2-hydroxyethyl)-N-methylfuranamide

HRID 726486

Reaction equation

HRID 726486 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11](Cl)=[O:12]>ClCCl>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:11]([C:7]1[O:6][CH:10]=[CH:9][CH:8]=1)=[O:12]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 682422-Furancarbonyl chloride

Product 1

HCID 15134402N-(2-hydroxyethyl)-N-methylfuranamideYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 115 g of 2-(methylamino)ethanol (1.53 mol.) and 500 ml of dichloromethane. The reaction flask was cooled with an ice bath. Next, 100 g of furoyl chloride (0.77 mol.) was slowly added via the addition funnel over 2.5 hours. The dichloromethane was washed with NaCl(aq.). Next, the NaCl(aq.) layer was extracted with dichloromethane and the two dichloromethane layers were combined and dried over MgSO4. The dichloromethane was removed with a rotoevaporator to yield 75 g (44%) of N-(2-hydroxyethyl)-N-methylfuranamide.

Workup

  1. customA one liter, three necked flask was equipped with overhead stirrer
  2. temperatureThe reaction flask was cooled with an ice bath
  3. washThe dichloromethane was washed with NaCl(aq.)
  4. extractionNext, the NaCl(aq.) layer was extracted with dichloromethane
  5. dry with materialdried over MgSO4
  6. customThe dichloromethane was removed with a rotoevaporator

Sources & evidence

ORD record
ord-31c376082b5049d5b79c2bfde065b44f
Source dataset
uspto-grants-1998_01
Patent number
US05709935

Linked notes

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