Water → N-(4-iodophenyl)-2-methylpropanamide

HRID 3667

Reaction equation

HRID 3667 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17].O>C(#N)C>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 108934-IodoanilineHCID 62325Isobutyryl chloride2×

Product 1

HCID 836020N-(4-iodophenyl)-2-methylpropanamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a dispersion of p-iodoaniline (219.0 g, 1 mol) in acetonitrile(1000 ml) was added pyridine (81.0 ml, 1 mol). Isobutyryl chloride (100.5 ml, 1 mol) was added dropwise to the mixture over 1 hour in an ice bath. The mixture was further stirred for one hour following the addition of isobutyryl chloride and to the mixture was added water (3000 ml). Precipitated crystalline solids were collected by filtration to give N-(4-iodophenyl)isobutyramide (281.7 g, Yield: 97%).

Workup

  1. filtrationPrecipitated crystalline solids were collected by filtration

Sources & evidence

ORD record
ord-1e9f35d9308c4443ac4377883641dd28
Source dataset
uspto-grants-1998_03
Patent number
US05734063

Linked notes

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