Potassium Iodide → HCID 22388411, compound

HRID 1072866Notes

Reaction equation

HRID 1072866 reaction equation
[C:1]([NH:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:14][NH:15][C:16](=O)[CH3:17])=[C:11]([CH:13]=1)[NH2:12])=[O:6])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:27][C:28]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:29]=1[CH2:30]Cl>CN(C)C=O.O>[ClH:27].[C:1]([NH:4][C:5]([C:7]1[CH:13]=[C:11]2[C:10]([CH2:14][N:15]=[C:16]([CH3:17])[N:12]2[CH2:30][C:29]2[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:28]=2[Cl:27])=[CH:9][CH:8]=1)=[O:6])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 22387946HCID 22387946, compound

Product 1

HCID 22388411HCID 22388411, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5-(Acetylcarbamoyl)-2-(acetylaminomethyl)aniline (1.06 g), potassium carbonate (1.40 g), potassium iodide (0.8 g) and 2,4-dichlorobenzyl chloride (1.40 g) in a mixture of dimethylformamide (15 ml) and water (10 ml) were stirred at 90° C. for 15 hr. After concentration of the reaction mixture, water was added and the mixture was extracted with ethyl acetate. The extract was concentrated, and methanol (5 ml) and concentrated hydrochloric acid (5 ml) were added. The mixture was refluxed for 1 hr. The reaction mixture was concentrated and purified by thin-layer chromatography to give the objective compound (0.46 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated
  3. additionmethanol (5 ml) and concentrated hydrochloric acid (5 ml) were added
  4. temperatureThe mixture was refluxed for 1 hr
  5. concentrationThe reaction mixture was concentrated
  6. custompurified by thin-layer chromatography

Sources & evidence

ORD record
ord-03b9d5c8368e4ab4ab9aaafd88fa0789
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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