Sodium hydride → HCID 21517173, compound

HRID 1283339Notes

Reaction equation

HRID 1283339 reaction equation
[C:1]1([N:7]2[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:19])[CH2:9][C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23][O:24][CH2:25][CH2:26]Br>O1CCCC1>[CH3:23][O:24][CH2:25][CH2:26][N:11]1[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:20])[CH2:9][C:10]1=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 89657Desmethylclobazam

Product 1

HCID 21517173HCID 21517173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

28.6 gm (0.1 mol) of 5-phenyl-7-chloro-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione were suspended in 750 ml of absolute tetrahydrofuran, 5 gm of a 50% dispersion of sodium hydride in tetrahydrofuran were added to the Suspension and the mixture was stirred for two hours at room temperature, whereby everything went into solution. 21-28 gm (0.15 - 0.2 mol) of β-bromo-ethyl methyl ether were then added to the solution, and the resulting mixture was refluxed for 15-20 hours. Thereafter, the reaction solution was evaporated in vacuo, residue was admixed with water, and the aqueous mixture was extracted with methylene chloride. The methylene chloride extract was vacuum-filtered to remove insoluble components, the filtrate was evaporated, and the residue was recrystallized from isopropyl ether, yielding 22 gm (64% of theory) of the compound of the formula ##SPC7##

Workup

  1. temperaturethe resulting mixture was refluxed for 15-20 hours
  2. customThereafter, the reaction solution was evaporated in vacuo, residue
  3. extractionthe aqueous mixture was extracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. filtrationwas vacuum-filtered
  6. customto remove insoluble components
  7. customthe filtrate was evaporated
  8. customthe residue was recrystallized from isopropyl ether
  9. customyielding 22 gm (64% of theory) of the compound of the formula

Sources & evidence

ORD record
ord-6ed43282203746f6ad8e80e652403775
Source dataset
uspto-grants-1976_08
Patent number
USRE028935

Reaction notes

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