Sodium Chloride → 8-chloro-1-[(diethyl amino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 903030Notes

Reaction equation

HRID 903030 reaction equation
[CH2:1]([N:3]([CH2:5][CH3:6])O)[CH3:2].[H-].[Na+].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]3[C:20]([CH2:23]Cl)=[N:21][N:22]=[C:18]3[CH2:17][N:16]=[C:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]=2[CH:31]=1.[Cl-].[Na+]>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]3[C:20]([CH2:23][N:3]([CH2:5][CH3:6])[CH2:1][CH3:2])=[N:21][N:22]=[C:18]3[CH2:17][N:16]=[C:15]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:14]=2[CH:31]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 19463DiethylhydroxylamineHCID 24758Sodium hydrideHCID 126123458-chloro-1-(chloromethyl)-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 126123578-chloro-1-[(diethyl amino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred, ice cold solution of N,N-diethylhydroxylamine (50 ml.) in dimethylformamide (50 ml.) under nitrogen, was treated with a 57% suspension of sodium hydride in mineral oil (1.39 g., 0.033 mole). The mixture was kept at ambient temperature for 55 minutes, cooled in an ice bath and treated with 8-chloro-1-(chloromethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (10.3 g., 0.03 mole). This mixture was kept at ambient temperature for 18 hours and poured into ice water. The resulting mixture was saturated with sodium chloride and extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was mixed with xylene and concentrated in vacuo, the resulting material was crystallized from wet methanol-ethyl acetate to give 8-chloro-1-[(diethylamino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine, N1 -oxide dihydrate in two crops: 5.91 g., of melting point 137.5°-139.5° C. dec. and 1.16 g., of melting point 135°-137.5° C. The analytical sample had a melting point of 135°-137.5° C. dec.

Workup

  1. temperaturecooled in an ice bath
  2. waitThis mixture was kept at ambient temperature for 18 hours
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionThe residue was mixed with xylene
  8. concentrationconcentrated in vacuo
  9. customthe resulting material was crystallized from wet methanol-ethyl acetate

Sources & evidence

ORD record
ord-32c3133e23a24d5486e2e319ebe55f70
Source dataset
uspto-grants-1980_10
Patent number
US04226772

Reaction notes

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