Allylamine → N-Allyl-2-iodobenzamide

HRID 49211

Reaction equation

HRID 49211 reaction equation
CN1CCOCC1.[CH2:8]([NH2:11])[CH:9]=[CH2:10].[I:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>C(#N)C>[CH2:8]([NH:11][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=1[I:12])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 79724-MethylmorpholineHCID 691122-Iodobenzoyl chloride

Product 1

HCID 2190306N-Allyl-2-iodobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

470 ml (4.28 mol) of N-methylmorpholine, followed by 224 ml (2.98 mol) of allylamine are added under ice cooling to 750 g (2.81 mol) of 2-iodo-benzoic acid chloride in 7.5 l of acetonitrile, and stirred for 60 min at RT. The precipitate is filtered off and the filtrate concentrated by evaporation on a RE. The residue of evaporation is dissolved in 4 l of EtOAc and 4 l of water, the water phase is separated and extracted twice with EtOAc. The organic phases are washed with water, 0.1 N HCl, water, sat. Na2CO3, water and brine, dried (Na2SO4) and concentrated by evaporation. Stirring of the residue in 2.5 l of hexane and filtering yields 2-iodo-benzoic acid allylamide; m.p. 105-106° C.

Workup

  1. filtrationThe precipitate is filtered off
  2. concentrationthe filtrate concentrated by evaporation on a RE
  3. customThe residue of evaporation
  4. dissolutionis dissolved in 4 l of EtOAc
  5. custom4 l of water, the water phase is separated
  6. extractionextracted twice with EtOAc
  7. washThe organic phases are washed with water, 0.1 N HCl, water, sat. Na2CO3, water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated by evaporation
  10. stirringStirring of the residue in 2.5 l of hexane
  11. filtrationfiltering

Sources & evidence

ORD record
ord-62c7c866bd5f45e0af5784edde849ebc
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Linked notes

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