Dimethylamine → N,N-dimethyl-5-methyl-2-iodophenylacetamide

HRID 1242232Notes

Reaction equation

HRID 1242232 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1[CH:6]=[CH:7][C:8]([I:15])=[C:9]([CH2:11][C:12](Cl)=[O:13])[CH:10]=1.CCOC(C)=O>CCOCC>[CH3:1][N:2]([CH3:3])[C:12](=[O:13])[CH2:11][C:9]1[CH:10]=[C:5]([CH3:4])[CH:6]=[CH:7][C:8]=1[I:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 219386685-Methyl-2-iodophenylacetyl chloride

Product 1

HCID 15541938N,N-dimethyl-5-methyl-2-iodophenylacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethylamine (200 ml of 2 M solution in THF) is added dropwise to a solution of 5-methyl-2-iodophenylacetyl chloride in Et2O (500 ml) which is cooled in an ice bath. After the addition is complete, EtOAc (350 ml) is added and the solution is washed with water (350 ml), brine (250 ml) and dried (MgSO4). Evaporation on a rotovap and trituration with 1:1 Et2O/hexanes gives N,N-dimethyl-5-methyl-2-iodophenylacetamide as a light tan solid, m.p. 47–49°.

Workup

  1. temperatureis cooled in an ice bath
  2. additionAfter the addition
  3. washthe solution is washed with water (350 ml), brine (250 ml)
  4. dry with materialdried (MgSO4)
  5. customEvaporation on a rotovap and trituration with 1:1 Et2O/hexanes

Sources & evidence

ORD record
ord-b49ba43e07dd4078bbb8b1f5c443386c
Source dataset
uspto-grants-2006_10
Patent number
US07115662B2

Reaction notes

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