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

HRID 1379985Notes

Reaction equation

HRID 1379985 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-8d56d972c56a4edeba0bf00a5a445d8c
Source dataset
uspto-grants-1986_04
Patent number
US04579581

Reaction notes

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