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

HRID 1280836Notes

Reaction equation

HRID 1280836 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-4fa8047affa7417691f1425538854708
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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