Sodium Hydroxide → HCID 12472016, compound

HRID 2397531Notes

Reaction equation

HRID 2397531 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]3[C:14]([CH2:17]Cl)=[N:15][N:16]=[C:7]3[C:6]=2[CH:19]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[OH-].[Na+]>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]3[C:14]([CH2:17][N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)=[N:15][N:16]=[C:7]3[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 12471994HCID 12471994, compound

Product 1

HCID 12472016HCID 12472016, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

10-Chloro-3-(chloromethyl)-7-methyl-5H-s-triazolo[4,3-d][1,4]benzodiazepin-6(7H)-one (5 g, prepared as described in Example 9) is suspended in 50 ml of 1,2-dimethoxyethane. N-methylpiperazine (5.4 g) is added to the suspension and the mixture is heated under reflux for 5 hours. The solvent is stripped off, 3N aqueous sodium hydroxide is added to the residue and the mixture is extracted with several portions of chloroform. The combined chloroform extracts are dried over sodium sulfate and the solvent is removed under vacuum to leave a residue which is recrystallized from absolute ethanol to yield 4 g of the title compound, melting point 228.5°-230.5° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. extractionthe mixture is extracted with several portions of chloroform
  4. dry with materialThe combined chloroform extracts are dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customto leave a residue which
  7. customis recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-00978f4030794634b77de50df596aafa
Source dataset
uspto-grants-1977_05
Patent number
US04022765

Reaction notes

Loading…