Allylamine → 3-fluoro-N-allylcinnamamide

HRID 1448112Notes

Reaction equation

HRID 1448112 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](Cl)=[O:8].[CH2:13]([NH2:16])[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([NH:16][CH2:13][CH:14]=[CH2:15])=[O:8]

Participants

5

Reactant 2

HCID 7853AllylamineHCID 2759064HCID 2759064, compound

Product 1

HCID 545159713-fluoro-N-allylcinnamamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-fluorocinnamoyl chloride (3.7 g) in dry toluene (35 ml) was added with stirring to allylamine (8 ml) in dry benzene (100 ml). The reaction mixture was allowed to stand at room temperature for three days. After evaporation of the solvents under reduced pressure the residue was triturated with water containing a small amount of sodium carbonate and washed with water. Recrystallization from ethanol: water gave 3-fluoro-N-allylcinnamamide (3.3 g), m.p. 84.5-87° C. as fine white needles. Elemental analysis, nmr and ir spectra were consistent with the structure assignment.

Workup

  1. customAfter evaporation of the solvents under reduced pressure the residue
  2. customwas triturated with water containing a small amount of sodium carbonate
  3. washwashed with water
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-8e16d01c7ffc413d9434011f51d17eab
Source dataset
uspto-grants-1979_12
Patent number
US04179524

Reaction notes

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