Methyl iodide → 1H-1,4-Benzodiazepine

HRID 441398

Reaction equation

HRID 441398 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]3C(CON)=NN=[C:10]3[CH2:9][N:8]=[C:7](C3C=CC=CC=3)[C:6]=2[CH:24]=1.[H-].[Na+].CI>CN(C)C=O>[NH:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:24][C:6]=2[CH:7]=[N:8][CH:9]=[CH:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 126124268-chloro-1-[(aminooxy)methyl]6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 1484311H-1,4-Benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 8-chloro-1-[(aminooxy)methyl]6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (0.02 mole) in dry dimethylformamide (50 ml.) is cooled in an ice bath under nitrogen and treated successively with a 57% mineral oil suspension of sodium hydride (0.84 g,. 0.02 mole) and methyliodide (0.02 mole). The mixture is allowed to come slowly to ambient temperature and stand for 18 hours. It is then concentrated in vacuo. The residue is chromatographed on silica gel with methanol to give 8-chloro-1-[[(methylamino)oxy]methyl]6-phenyl-4H-s-triazolo]4,3-a][1,4]benzodiazepine.

Workup

  1. customto come slowly to ambient temperature
  2. concentrationIt is then concentrated in vacuo
  3. customThe residue is chromatographed on silica gel with methanol

Sources & evidence

ORD record
ord-d01ab87d9aa44073b1d7ec8d3cec7ccd
Source dataset
uspto-grants-1977_08
Patent number
US04039551

Linked notes

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