Sodium Iodide → HCID 19608176, compound

HRID 1291626Notes

Reaction equation

HRID 1291626 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)=[O:12].[C:37]([O-:40])(=[O:39])[CH3:38].[Na+].[I-].[Na+]>C(O)(=O)C>[C:37]([O:40][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)=[O:12])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 517045Sodium AcetateHCID 19608161HCID 19608161, compound

Product 1

HCID 19608176HCID 19608176, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-{4-[2-(6-bromohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (2.00 g), sodium acetate (0.36 g), sodium iodide (0.55 g) and acetic acid (20 ml) is refluxed for 1 day. The solvent is distilled off and the resulting residue is extracted with ethyl acetate. The organic layer is washed successively with 2N aqueous sodium hydroxide solution and saturated saline solution, and dried over magnesium sulfate. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=500:1), and recrystallized from ethanol to give 1-{4-[2-(6-acetyloxyhexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (1.07 g) as white powder, m.p. 145°-146° C.

Workup

  1. temperatureis refluxed for 1 day
  2. distillationThe solvent is distilled off
  3. extractionthe resulting residue is extracted with ethyl acetate
  4. washThe organic layer is washed successively with 2N aqueous sodium hydroxide solution and saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent is concentrated
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=500:1)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-461cdca0517f4440ac715d752bbc2a4b
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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