Sodium Iodide → HCID 17830867, compound

HRID 478367Notes

Reaction equation

HRID 478367 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([NH:21][C:22](=[O:25])[CH2:23]Cl)[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:34]1([OH:44])[C:43]2[CH2:42][CH2:41][CH2:40][CH2:39][C:38]=2[CH:37]=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:20]=[C:19]([NH:21][C:22](=[O:25])[CH2:23][O:44][C:34]2[CH:35]=[CH:36][CH:37]=[C:38]3[C:43]=2[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 18001078HCID 18001078, compound

Product 1

HCID 17830867HCID 17830867, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

1-[2-Methyl-4-(2-chloroacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.8 g) is dissolved in dimethylformamide (5 ml), and thereto are added potassium carbonate (0.47 g), sodium iodide (0.51 g) and 5,6,7,8-tetrahydro-1-naphthol (0.40 g), and the mixture is stirred at 60° C. for three hours. To the reaction solution is added ethyl acetate, and the mixture is washed with a saturated aqueous potassium hydrogen sulfate solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The resulting residue is allowed to stand for one day, washed with dichloromethane, filtered, and dried to give 1-{2-methyl-4-[2-(5-tetrahydronaphthyloxy)acetylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.72 g) as white powder.

Workup

  1. washthe mixture is washed with a saturated aqueous potassium hydrogen sulfate solution
  2. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. waitto stand for one day
  6. washwashed with dichloromethane
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-215a1deb875342d09aaea70357d61ab1
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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