Butyrohydrazide → 9-Bromo-6-(4-nitrophenyl)-8-methoxy-3-propyl-11h-[1,2,4]triazolo[4,3-c][2,3]benzodiazepine

HRID 430654

Reaction equation

HRID 430654 reaction equation
[Br:1][C:2]1[C:3]([O:24][CH3:25])=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][N:9]=[C:8](SC)[CH2:7][C:6]=2[CH:23]=1.[C:26]([NH:31][NH2:32])(=O)[CH2:27][CH2:28][CH3:29]>CN(C=O)C.Cl>[Br:1][C:2]1[C:3]([O:24][CH3:25])=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][N:9]3[C:26]([CH2:27][CH2:28][CH3:29])=[N:31][N:32]=[C:8]3[CH2:7][C:6]=2[CH:23]=1

Participants

5

Reactant 2

HCID 77079ButyrohydrazideHCID 181831987-Bromo-8-methoxy-4-methylthio-1-(4-nitrophenyl)-5h-2,3-benzodiazepine

Product 1

HCID 181831899-Bromo-6-(4-nitrophenyl)-8-methoxy-3-propyl-11h-[1,2,4]triazolo[4,3-c][2,3]benzodiazepineYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
112.5 °C

Procedure

1.17 g (2.78 mmol) of the compound of step B is dissolved in 40 ml of anhydrous DMF and mixed with 0.73 g (8.4 mmol) of butyric acid hydrazide as well as 3 drops of concentrated HCl. The mixture is stirred for 5 hours at 110-115° C. Then, the mixture is poured onto ice (160 g) and stirred for 1 more hour. The precipitated crystals are suctioned off and washed with water. 1.05 g (83%) of 9-bromo-6-(4-nitrophenyl)-8-methoxy-3-propyl-11H-[1,2,4]triazolo(4,3-c][2,3]benzodiazepine with a melting point of 238-240° C. is obtained.

Workup

  1. additionThen, the mixture is poured onto ice (160 g)
  2. stirringstirred for 1 more hour
  3. washwashed with water

Sources & evidence

ORD record
ord-728f87f35c844e35992bb1586774ce43
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Linked notes

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