Furfurylamine → N-(furan-2-ylmethyl)furan-2-carboxamide

HRID 582438Notes

Reaction equation

HRID 582438 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](Cl)=[O:21].ClCCl>CCCCCC.C(OCC)(=O)C>[CH2:1]([NH:7][C:20]([C:16]1[O:15][CH:19]=[CH:18][CH:17]=1)=[O:21])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 22096625HCID 22096625, compound

Product 1

HCID 4528178N-(furan-2-ylmethyl)furan-2-carboxamide

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-furfuryl-2-furamide was prepared by adding dropwise to a mixture of furfurylamine (7.44 g; 7 mmol; ex Aldrich) and triethylamine (35.6 g; 352 mmol) in dichloromethane 2-furoyl chloride (23 g; 176 mmol) at a temperature of 0 to 5° C. The product obtained was washed with water, dried with magnesium sulphate and evaporated. Subsequently, the product so obtained was purified by flash chromatography (silica, hexane/ethyl acetate as eluant) and 14 g (97% yield) of the product was recovered.

Workup

  1. customThe product obtained
  2. washwas washed with water
  3. dry with materialdried with magnesium sulphate
  4. customevaporated
  5. customSubsequently, the product so obtained

Sources & evidence

ORD record
ord-4b1b2df97d6b43e0b1a245a2a206a9ec
Source dataset
uspto-grants-1999_07
Patent number
US05925152

Reaction notes

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