2-Bromoethyldimethylamine → 4-(2-Dimethylaminoethyl)-1-methyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a] [1,5]benzodiazepin-5-one

HRID 261236Notes

Reaction equation

HRID 261236 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:8]=3[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10](=[O:12])[CH2:11][C:5]2=[N:4][N:3]=1.[H-].[Na+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Br>COCCOC>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][CH:11]1[C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:7]=2[N:6]2[C:2]([CH3:1])=[N:3][N:4]=[C:5]12

Participants

5

Reactant 3

HCID 178642-BromoethyldimethylamineHCID 24758Sodium hydrideHCID 122643201-methyl-8-chloro-6-phenyl-4H-s-triazolo-[4,3-a][1,5]benzodiazepin-5-one

Product 1

HCID 203293314-(2-Dimethylaminoethyl)-1-methyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a] [1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

37.0 g of 1-methyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,5]benzodiazepin-5-one and 7.8 g of a 50 percent sodium hydride mineral oil dispersion in 400 ml of dry 1,2-dimethoxyethane are stirred for 2 hours. A solution of 13.7 g of 2-dimethylaminoethyl bromide in 40 ml of dry 1,2-dimethoxyethane is added and the whole is stirred for 18 hours. The solvent is evaporated and the residue is partitioned between methylene chloride and water. The organic phase is washed with water, dried and evaporated to give the title compound.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between methylene chloride and water
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-48808cb63b8347cbbc8304689ba19aa0
Source dataset
uspto-grants-1979_08
Patent number
US04164580

Reaction notes

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