Triethylamine → Rac. 2-iodo-benzoic acid-(1-oxo-prop-2-yl-amide)

HRID 2252853Notes

Reaction equation

HRID 2252853 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[I:13])[CH3:4].C(N(CC)CC)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>CS(C)=O.O>[O:1]=[CH:2][CH:3]([NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[I:13])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 43418915HCID 43418915, compound

Product 1

HCID 87734531Rac. 2-iodo-benzoic acid-(1-oxo-prop-2-yl-amide)

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of 54.9 g (345 mmol) of sulfur trioxide-pyridine complex in 150 ml of DMSO is added dropwise at RT to 35 g (115 mmol) of rac. 2-iodo-benzoic acid-(1-hydroxy-prop-2-yl-amide) in 50 ml of DMSO and 48 ml (345 mmol) of triethylamine. After 10 min, the mixture is poured onto 0.4 l of EtOAc, 0.21 of sat. NaHCO3 solution and 0.2 l of water, the aqueous phase is separated and extracted 4 more times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form rac. 2-iodo-benzoic acid-(1-oxo-prop-2-yl-amide).

Workup

  1. customthe aqueous phase is separated
  2. extractionextracted 4 more times with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-27a32932248f4812a3fc42cdda0e2d17
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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