Acetic Anhydride → N-(4-iodophenethyl)acetamide

HRID 76157Notes

Reaction equation

HRID 76157 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>CN(C1C=CN=CC=1)C.C1COCC1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 151501452-(4-Iodophenyl)ethylamine

Product 1

HCID 66634968N-(4-iodophenethyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.00 g (12.1 mmol) 4-iodophenethylamine and 0.37 g (3.03 mmol) DMAP in 50 mL THF are cooled down to 0° C. 4.95 g (48.5 mmol) acetic anhydride are added and, after removing of the cooling bath, the reaction mixture is stirred for 5 h at r.t. The reaction mixture is quenched in ice cold water and extracted with EtOAc. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 98.5/1.5).

Workup

  1. customafter removing of the cooling bath
  2. customThe reaction mixture is quenched in ice cold water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer is dried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 98.5/1.5)

Sources & evidence

ORD record
ord-16669a0397984d15a494644914e4ddfe
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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