Pyridine → 3-(2-Bromophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine

HRID 2209418Notes

Reaction equation

HRID 2209418 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1C(Cl)=O.[Br:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([NH:17][NH2:18])=O.C[N:24]([CH3:27])C=O.[N:28]1C=CC=CC=1>O>[Br:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]1[N:28]=[N:24][C:27]([C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])=[N:18][N:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 874382,6-Difluorobenzoyl chlorideHCID 1014602-Bromobenzohydrazide

Product 1

HCID 233627443-(2-Bromophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.94 g (1.05 equivalent) of 2,6-difluorobenzoyl chloride is added dropwise to a mixture containing 1.1 g of (2-bromobenzoyl)hydrazine, 3 ml of dimethylformamide and 0.5 ml of pyridine under cooling. The suspension obtained is stirred at room temperature for 30 minutes, then poured into water. The solid precipitate is separated by filtration and dried to give the desired product as white crystals in a yield of 1.35 g.

Workup

  1. temperatureunder cooling
  2. customThe suspension obtained
  3. customThe solid precipitate is separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-20b9333f79ee404984ce525a23670795
Source dataset
uspto-grants-1995_10
Patent number
US05455237

Reaction notes

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