Pyridine → 2-Iodo-5-[(2-phenylbutanoyl)amino]benzamide

HRID 503688Notes

Reaction equation

HRID 503688 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[C:12]1([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.C(OCC)(=O)C>ClCCl>[I:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19](=[O:20])[CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][CH3:23])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 981732-Phenylbutyryl chlorideHCID 155476225-Amino-2-iodobenzamide

Product 1

HCID 594284852-Iodo-5-[(2-phenylbutanoyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.823 g (3.14 mmol) of the compound from Example 4A are dissolved in 10 ml of dichloromethane at RT, and 0.688 mg (3.77 mmol) of 2-phenylbutyryl chloride and 0.298 mg (3.77 mmol) of pyridine are added. The mixture is stirred at RT over after. Ethyl acetate is added, and the mixture is extracted with water. The organic phases are dried over magnesium sulfate and freed of solvent under reduced pressure. The residue is purified by chromatography on a silica gel column (mobile phase ethyl acetate:cyclohexane 2:1). 0.943 g (72% of theory) of product are obtained.

Workup

  1. extractionthe mixture is extracted with water
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. customThe residue is purified by chromatography on a silica gel column (mobile phase ethyl acetate:cyclohexane 2:1)
  4. custom0.943 g (72% of theory) of product are obtained

Sources & evidence

ORD record
ord-12afdde820d246bf97048a1258ddd711
Source dataset
uspto-grants-2010_08
Patent number
US07776922B2

Reaction notes

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