Triethylamine → N-(2-Furylmethoxy)phthalimide

HRID 1451555Notes

Reaction equation

HRID 1451555 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH2:13](Cl)[C:14]1[O:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:13]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:14]1[O:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 2195202-(Chloromethyl)furan

Product 1

HCID 19975015N-(2-Furylmethoxy)phthalimideYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

43.5 g of N-hydroxyphthalimide were added to a solution of 31.1 g of furfuryl chloride in 80 ml of dimethylformamide, and the mixture was cooled to 0° C. 40.6 ml of triethylamine were then added dropwise to the mixture, after which the reaction mixture was stirred at 0° C. for 2 hours and then at room temperature for 24 hours. At the end of this time, the reaction mixture was poured into ice-water. The resulting colorless crystals were collected by filtration, to afford 53.1 g of N-furfuryloxyphthalimide, melting at 145-147° C.

Workup

  1. waitat room temperature for 24 hours
  2. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-813a3886d9e04621a5524eaf3ca1dd56
Source dataset
uspto-grants-1997_02
Patent number
US05604256

Reaction notes

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