4-Iodoaniline → HCID 178451098, compound

HRID 1170454Notes

Reaction equation

HRID 1170454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:21])[C:9](=[CH:17][N:18]([CH3:20])C)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[I:22][C:23]1[CH:29]=[CH:28]C(N)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:21])[C:9](=[CH:17][NH:18][C:20]1[CH:28]=[CH:29][C:23]([I:22])=[CH:24][CH:25]=1)[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

Participants

4

Reactant 2

HCID 108934-IodoanilineHCID 68689778HCID 68689778, compound

Product 1

HCID 178451098HCID 178451098, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,1-dimethylethyl 2-chloro-α-[(dimethylamino)methylene]-β-oxo-benzenepropanoate (25.5 mg, 0.082 mmol) in 1 mL of toluene was treated with 4-iodoaniline (17.9 mg, 0.082 mmol) added as a solid in one portion. After stirring overnight, the reaction was concentrated in vacuo and the residue was adsorbed onto silica gel and added to 19.5 cm of flash silica in a 2 cm dia. column. Elution with 5:1 hexanes/EtOAc gave the title compound as a solid.

Workup

  1. additionadded as a solid in one portion
  2. concentrationthe reaction was concentrated in vacuo
  3. additionadded to 19.5 cm of flash silica in a 2 cm dia
  4. washElution with 5:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-d3f542eeaad740ba805906a3b09fa5ad
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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