Potassium Iodide → HCID 19608059, compound

HRID 1291679Notes

Reaction equation

HRID 1291679 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:40][C:41]([NH2:43])=[O:42]>CC(C)=O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH2:40][C:41](=[O:42])[NH2:43])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 19607777HCID 19607777, compound

Product 1

HCID 19608059HCID 19608059, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-oxo-1-[4-(2-hydroxybenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (400 mg) in acetone (20 ml) are added potassium carbonate (210 mg), potassium iodide (250 mg) and 2-chloroacetamide (120 mg), and the mixture is refluxed for 2 hours. The insoluble materials are removed by filtration, and the filtrate is distilled off. Dichloromethane is added to the resulting residue, and the mixture is washed with saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is recrystallized from ethyl acetate/n-hexane to give 5-oxo-1-[4-(2-carbamoylmethoxybenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (436 mg) as white powder, m.p. 226°-228° C.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customThe insoluble materials are removed by filtration
  3. distillationthe filtrate is distilled off
  4. additionDichloromethane is added to the resulting residue
  5. washthe mixture is washed with saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a1c9a97caa424b97aa323e584e44597f
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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