Sodium Iodide → HCID 17830871, compound

HRID 478361Notes

Reaction equation

HRID 478361 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:22])[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=3[O:20][CH3:21])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:6]=2[CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br-].[Br-].[C:37]1([CH3:44])[C:38]([CH3:43])=[CH:39][CH:40]=[CH:41][CH:42]=1.[I-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:22])[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:43][C:38]5[C:37](=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:44]4)=[CH:15][C:14]=3[O:20][CH3:21])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:6]=2[CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 18001039HCID 18001039, compoundHCID 22258337HCID 22258337, compound

Product 1

HCID 17830871HCID 17830871, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 7-chloro-5-methoxycarbonylmethyl-1-(2-methoxy-4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (2.6 g) in ethanol (100 ml) are added sodium carbonate (1.5 g), o-xylene dibromide (1.87 g) and sodium iodide (2.42 g), and the mixture is stirred at 60-70° C. for three hours. The mixture is evaporate to remove the solvent, and to the residue is added water, and the mixture is extracted with ethyl acetate. The extract is dried, and evaporate to remove the solvent. The residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:10→1:5) to give 7-chloro-5-methoxycarbonylmethyl-1-[2-methoxy-4-(2-isoindolinyl)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.32 g) as colorless amorphous.

Workup

  1. customThe mixture is evaporate
  2. customto remove the solvent
  3. additionto the residue is added water
  4. extractionthe mixture is extracted with ethyl acetate
  5. customThe extract is dried
  6. customevaporate
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:10→1:5)

Sources & evidence

ORD record
ord-474a364bd12349849cf63d0bcc97809b
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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