Dimethylformamide → HCID 21223277, compound

HRID 1939142Notes

Reaction equation

HRID 1939142 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[OH:8][CH2:9][C:10]1[O:15][CH2:14][N:13]([C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[C:12](=[O:25])[C:11]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CI>O>[CH3:3][O:8][CH2:9][C:10]1[O:15][CH2:14][N:13]([C:16]([CH3:17])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:24])[C:12](=[O:25])[C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21223285HCID 21223285, compound

Product 1

HCID 21223277HCID 21223277, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in oil, 0.11 g) was suspended in diformaldahyde (2 ml), cooled with ice; then a dimethylformamide solution (6 ml) of 6-hydroxymethyl-3-(1-methyl-1-phenylethyl)-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-one (Compound No. 53, 0.8 g) was added slowly thereto. After stirring the mixture, methyl iodide (0.71 g) was added, and the mixture was stirred again at room temperature. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was rinsed with saturated saline solution, and dried with magnesium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography to afford the captioned compound (0.56 g, yield 67%).

Workup

  1. temperaturecooled with ice
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was rinsed with saturated saline solution
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ebd89c1eafe243d0aea5375e0c3b9e94
Source dataset
uspto-grants-1997_12
Patent number
US05696054

Reaction notes

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