Dimethylformamide → HCID 12785887, compound

HRID 1075211Notes

Reaction equation

HRID 1075211 reaction equation
C(=O)(O)[O-].[Na+].[Cl-].[OH:7][NH3+:8].[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=S)[CH2:17][N:16]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:14]=2[CH:27]=1.[CH3:28][N:29](C)[CH:30]=[O:31]>O1CCOCC1>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]=[C:18]([NH:8][O:7][C:30](=[O:31])[NH:29][C:28]3[CH:12]=[CH:11][CH:10]=[CH:27][CH:14]=3)[CH2:17][N:16]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:14]=2[CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 21645Hydroxylamine HCl2×HCID 516892Sodium Bicarbonate2×HCID 126123797-Bromo-5-(pyridin-2-yl)-1,3-dihydro-2H-1,4-benzodiazepine-2-thione

Product 1

HCID 12785887HCID 12785887, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of sodium bicarbonate and 0.8 g of hydroxylammonium chloride are added to 3 g of 7-bromo-5-(2-pyridyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-thione in 60 ml of dioxane containing dimethylformamide and the mixture is stirred for 8 hours. 0.3 g of sodium bicarbonate and 0.25 g of hydroxylammonium chloride are again added and the mixture is stirred for 30 minutes at 50° C. The mixture is filtered off under suction when cold, and 1.0 ml of phenylisocyanate is added to the filtrate which is stirred for 1 hour. After the usual working up process, 1.6 g of colorless crystals are precipitated and are recrystallized from ethanol. Melting point 190° to 192° C.

Workup

  1. stirringthe mixture is stirred for 30 minutes at 50° C
  2. filtrationThe mixture is filtered off under suction when cold
  3. addition1.0 ml of phenylisocyanate is added to the filtrate which
  4. stirringis stirred for 1 hour
  5. customare precipitated
  6. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-9adc53b52b5440d68b3029518eec562c
Source dataset
uspto-grants-1983_07
Patent number
US04395409

Reaction notes

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