Dimethylformamide → HCID 12785863, compound

HRID 1075207Notes

Reaction equation

HRID 1075207 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[CH3:20][N:21](C)[CH:22]=[O:23].C(=O)(O)[O-].[Na+].[Cl-:30].[OH:31][NH3+:32]>O1CCOCC1>[Cl:30][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:32][O:31][C:22](=[O:23])[NH:21][C:20]3[CH:4]=[CH:3][CH:2]=[CH:19][CH:6]=3)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 826706Thionordiazepam

Product 1

HCID 12785863HCID 12785863, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.5 g of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione are suspended in 125 ml of dioxane and 50 ml of dimethylformamide and 2.2 g of sodium bicarbonate and 1.8 g of hydroxylammonium chloride are added to the suspension. After stirring for 8 hours at room temperature (monitoring by thin layer chromatography), the mixture is filtered off under suction and 2.8 ml of phenylisocyanate are added to the filtrate. After stirring for 30 minutes, the reaction mixture is added dropwise into 200 ml of water and the mixture is filtered off under suction. Recrystallization from ethanol/dimethylformamide yields colorless crystals of melting point 215°-217° C. Yield 4.6 g.

Workup

  1. filtrationthe mixture is filtered off under suction and 2.8 ml of phenylisocyanate
  2. additionare added to the filtrate
  3. stirringAfter stirring for 30 minutes
  4. additionthe reaction mixture is added dropwise into 200 ml of water
  5. filtrationthe mixture is filtered off under suction
  6. customRecrystallization from ethanol/dimethylformamide
  7. customyields colorless crystals of melting point 215°-217° C

Sources & evidence

ORD record
ord-1f2c8f2c600c48818e1a4ec598dfd8fd
Source dataset
uspto-grants-1983_07
Patent number
US04395409

Reaction notes

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