Dimethylformamide → HCID 23037982, compound

HRID 1163974Notes

Reaction equation

HRID 1163974 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH2:13][C:12]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[N:11]1.CN(C)C=O.[Br:33]Br>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([Br:33])[C:12]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[N:11]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24408BromineHCID 113055Benzamide, N-[4,5-dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-3-nitro-

Product 1

HCID 23037982HCID 23037982, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

428 g (1.0 mol) of 1-(2,4,6-trichlorophenyl)-3-(3-nitrobenzamido)-5-oxo-2-pyrazoline was added to 2.2 liters of dimethylformamide. To the solution, there was added dropwise 160 g (1.0 mol) of bromine with stirring while cooling with ice, and after stirring for about 1 hour, the reaction solution was poured into 9 liters of water. The crystals thus-separated were collected by filtration to obtain 489.5 g (96.6% yield) of 1-(2,4,6-trichlorophenyl)-3-(3-nitrobenzamido)-4-bromo-5-oxo-2-pyrazoline.

Workup

  1. temperaturewhile cooling with ice
  2. stirringafter stirring for about 1 hour
  3. customThe crystals thus-separated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3c1c8b76df9b466ca372bba73f687fd3
Source dataset
uspto-grants-1983_01
Patent number
US04367282

Reaction notes

Loading…