Potassium Carbonate → N-Crotyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

HRID 2108565Notes

Reaction equation

HRID 2108565 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[CH:25]=[CH:26][CH3:27]>CN(C)C=O.CCOC(C)=O>[CH2:24]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])[C:3](=[O:4])[C:2]([F:16])([F:1])[F:17])[CH:25]=[CH:26][CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

Product 1

HCID 86611334N-Crotyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamineYield 36.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-2-iodo-4-chlorophenethylamine (6.2 g, 15.8 mmol) in dimethylformamide (350 mL) was treated with K2CO3 (15.8 g, 114 mmol) and crotyl bromide (6.0 g, 44 mmol) sequentially, the mixture was stirred at 60 C for 16 hours and then cooled to 20 C. The mixture was diluted with EtOAc (350 mL), washed with water (3×300 mL), dried with Na2SO4 and concentrated. Flash chromatography (5-15% EtOAc in hexane) resulted in 2.5 g of a clear oil. MS calculated for C14H14ClF3INO+H: 432, observed: 432.

Workup

  1. temperaturecooled to 20 C
  2. washwashed with water (3×300 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e227eed5404b4b26b60790a8416bdc4d
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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