Aniline → N-Phenyl-2-furancarboxamide

HRID 582440

Reaction equation

HRID 582440 reaction equation
[NH2:1][C:2]1[CH:7]=[CH: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>[C:2]1([NH:1][C:20]([C:16]2[O:15][CH:19]=[CH:18][CH:17]=2)=[O:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 682422-Furancarbonyl chloride

Product 1

HCID 220406N-Phenyl-2-furancarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

N-phenyl furamide was prepared by adding to a mixture of aniline (23.3 g; 250 mmol) and triethylamine (25.3 g; 250 mmol) in dichloromethane slowly 32.6 g (250 mmol) of 2-furoyl chloride, while maintaining the temperature at -10° C. The product obtained was washed with diluted hydrochloric acid and water, dried with magnesium sulphate and evaporated. The product so obtained was than triturated with hexane and filtered. 39.3 g (84% yield of product was recovered.

Workup

  1. customThe product obtained
  2. washwas washed with diluted hydrochloric acid and water
  3. dry with materialdried with magnesium sulphate
  4. customevaporated
  5. customThe product so obtained
  6. customthan triturated with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ec294cbabf8b4576be6a8b4d93a811ec
Source dataset
uspto-grants-1999_07
Patent number
US05925152

Linked notes

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