Allyl bromide → HCID 20135066, compound

HRID 580388Notes

Reaction equation

HRID 580388 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][O:15][CH3:16])[C:12](=[O:17])[CH:11]([C:18]([O:20][CH3:21])=[O:19])[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:9][C:8]=2[CH:30]=1.[CH2:31](Br)[CH:32]=[CH2:33]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][O:15][CH3:16])[C:12](=[O:17])[C:11]([C:18]([O:20][CH3:21])=[O:19])([CH2:33][CH:32]=[CH2:31])[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:9][C:8]=2[CH:30]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 20135077HCID 20135077, compound

Product 1

HCID 20135066HCID 20135066, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 50% sodium hydride (48 mg; 1 mmole) in dimethylformamide (5 ml) cooled at 0°-5° C. was added dropwise a solution of 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-1-(methoxymethyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (102 mg; 0.25 mmole) in dimethylformamide (1 ml). After stirring at 0°-5° C. for 20 minutes, allyl bromide (360 μl ; 4 mmole) was added dropwise, and the reaction mixture was allowed to stir at 0° C. to room temperature for two hours. Excess sodium hydride was destroyed with water, and the mixture was extracted with ether. The aqueous layer was extracted with ether (two times), and the combined organic layers were dried (magnesium sulfate) and concentrated. The crude residue was triturated with hexane (20 ml) to obtain 93 mg of white, crystalline title compound. [The mother liquor contained additional product].

Workup

  1. temperaturecooled at 0°-5° C.
  2. stirringto stir at 0° C. to room temperature for two hours
  3. customExcess sodium hydride was destroyed with water
  4. extractionthe mixture was extracted with ether
  5. extractionThe aqueous layer was extracted with ether (two times)
  6. dry with materialthe combined organic layers were dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe crude residue was triturated with hexane (20 ml)

Sources & evidence

ORD record
ord-52f8c10241834e5ea945be21bda9cb82
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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