Methyl iodide → HCID 15886887, compound

HRID 651581Notes

Reaction equation

HRID 651581 reaction equation
[CH2:1]([N:7]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:8]([CH:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].CI.[C:37](OCC)(=O)C>CN(C)C=O>[CH2:27]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]([CH:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:37])[C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11]1)=[O:9])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15886886HCID 15886886, compound

Product 1

HCID 15886887HCID 15886887, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg of N,N-dihexyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxamide in 10 ml of N,N-dimethylformamide was added 21 mg of 60% sodium hydride/oil, followed by stirring at room temperature for an hour. To the solution was added 33 μl of methyl iodide, followed by stirring at room temperature for 5 hours. The reaction solution, after addition of ethyl acetate, was washed with water, 1 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 155 mg of N,N-dihexyl-6,11-dihydro-11-methyl-5-thia-11-aza-benzo[a]fluoren-6-carboxamide.

Workup

  1. stirringby stirring at room temperature for 5 hours
  2. washwas washed with water, 1 N hydrochloric acid
  3. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-2ccb660d84be4522ba00a751f171d14e
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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