Water → HCID 68674316, compound

HRID 2196054Notes

Reaction equation

HRID 2196054 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7]C2N[C:13](=O)[CH2:12][C:11](=[O:16])[N:10]([CH3:17])[C:9]=2[CH:18]=1.[CH3:19]I.O.[CH3:22][N:23]([CH:25]=[O:26])[CH3:24]>C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:22]2[N:23]([CH3:24])[C:25](=[O:26])[C:12]([CH3:13])([CH3:19])[C:11](=[O:16])[N:10]([CH3:17])[C:9]=2[CH:18]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 669610818-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 68674316HCID 68674316, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 128 mg, 3.2 mmol) was suspended in DMF (10 ml). 8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (176 mg, 0.8 mmol) was added thereto at 0° C., and stirring was conducted at the same temperature for 1 hour. Methyl iodide (0.25 ml, 4.0 mmol) was added to the mixture, and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from n-hexane to thereby obtain 161.6 mg (yield: 77%) of 7-methoxy-1,3,3,5-tetramethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a white powder.

Workup

  1. stirringstirred at room temperature overnight
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-5cacb21e69a5415da9a026b116a7ab13
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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