Sodium Iodide → HCID 19608176, compound

HRID 745065Notes

Reaction equation

HRID 745065 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-d7e94f5463fb49ec84aa887bc749a73c
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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