Sodium hydride → HCID 11058980, compound

HRID 53898Notes

Reaction equation

HRID 53898 reaction equation
[NH:1]1[C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22][N:1]1[C:5]2[C:6](=[O:12])[N:7]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 3085877Aldisine

Product 1

HCID 11058980HCID 11058980, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 mg amount of the 6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione (aldisin) described in the reference (Prager, R. et al: Aust. J. Chem., 43, p. 355-365 (1990)) was added to a 20 ml dimethylformamide suspension of 252 mg of sodium hydride (60% oil). The mixture was stirred at room temperature for 1 hour. A 1.12 ml amount of trimethylsilylethoxymethyl chloride was added under ice cooling, the mixture was stirred at room temperature for 3 hours, then a saturated aqueous solution of ammonium chloride was added and extraction was performed by ethyl acetate. The extract was washed with saturated saline, dried, filtered, and concentrated under reduced pressure to obtain a residue which was purified by silica gel column chromatography (hexane:ether acetate=6:1) to obtain 623 mg of the above-referenced compound (8) (yield 48%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextraction
  3. washThe extract was washed with saturated saline
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas purified by silica gel column chromatography (hexane:ether acetate=6:1)

Sources & evidence

ORD record
ord-1c18622ef01b47798c68d59f65e97b4b
Source dataset
uspto-grants-1997_04
Patent number
US05621099

Reaction notes

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