Phthalimide → Desmethyladinazolam

HRID 268531Notes

Reaction equation

HRID 268531 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20]([CH2:21][N:22]3C(=O)[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=O)=[N:19][N:18]=[C:17]2[CH2:33][N:34]2C(=O)C3=CC=CC=C3C2=O)=[C:6]([CH:15]=1)C(C1C=CC=CC=1)=O.O.NN.C1(=O)NC(=O)C2=CC=CC=C12>C(O)C>[Cl:1][C:2]1[CH:15]=[CH:6][C:5]2[N:16]3[C:17]([CH2:33][NH2:34])=[N:18][N:19]=[C:20]3[CH2:21][N:22]=[C:23]([C:24]3[CH:25]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 24654Hydrazine hydrate (1:1)HCID 126119515-chloro-2-[3,5-bis(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone

Product 1

HCID 12611937Desmethyladinazolam

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 5-chloro-2-[3,5-bis(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone (1.81 g, 0.003 mole) and absolute ethanol (30 ml) is treated with hydrazine hydrate (0.437 ml, 0.009 mole) and kept in an oil bath at 72°-76°C for two hours and 20 minutes. During this period the phthalimide dissolves and a second solid forms. The mixture is cooled in an ice bath and filtered. The solid is washed with ethanol and methylene chloride. The filtrate is concentrated in vacuo. This residue is mixed with cold water and extracted with chloroform. The extract is washed (brine), dried over anhydrous sodium sulfate and concentrated in vacuo to give 8-chloro-1-(aminomethyl)-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine as a crude oil.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. filtrationfiltered
  3. washThe solid is washed with ethanol and methylene chloride
  4. concentrationThe filtrate is concentrated in vacuo
  5. additionThis residue is mixed with cold water
  6. extractionextracted with chloroform
  7. washThe extract is washed (brine)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47a07926f0bd42808ef90a2149c29b66
Source dataset
uspto-grants-1976_03
Patent number
US03947466

Reaction notes

Loading…