Sodium Hydroxide → HCID 12472016, compound

HRID 918063Notes

Reaction equation

HRID 918063 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, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5 g. of 10-chloro-3-(chloromethyl)-7-methyl-5H-s-triazolo-[4,3-d][1,4]benzodiazepin-6(7H)-one from part (a) 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°.

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
  8. customto yield 4 g

Sources & evidence

ORD record
ord-1cfc49acd9f8448eb343594f6a50a456
Source dataset
uspto-grants-1976_07
Patent number
US03969366

Reaction notes

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