Furfurylamine → 3,5-dichloro-N-(furan-2-ylmethyl)benzamide

HRID 543797Notes

Reaction equation

HRID 543797 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14](Cl)=[O:15]>C(OCC)(=O)C.O>[CH2:1]([NH:7][C:14](=[O:15])[C:13]1[CH:12]=[C:11]([Cl:10])[CH:19]=[C:18]([Cl:20])[CH:17]=1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3438FurfurylamineHCID 14798Sodium HydroxideHCID 761913,5-Dichlorobenzoyl chloride

Product 1

HCID 23231223,5-dichloro-N-(furan-2-ylmethyl)benzamideYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a vigorously stirred solution of furfurylamine (2.78 g) in ethyl acetate (40 ml) was added sodium hydroxide (1.15 g) in water (45 ml), followed immediately by the addition of a solution of 3,5-dichlorobenzoyl chloride (6.0 g) in ethyl acetate (20 ml). Following the mild exothermic reaction the ethyl acetate layer was removed, dried (MgSO4), and evaporated. Crystallisation of the residue from cyclohexane gave the product (6.6 g) as colourless needles.

Workup

  1. customwas removed
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customCrystallisation of the residue from cyclohexane

Sources & evidence

ORD record
ord-01e8b0e8468343628ccab2b2b494871a
Source dataset
uspto-grants-1984_05
Patent number
US04447446

Reaction notes

Loading…