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

HRID 2209419Notes

Reaction equation

HRID 2209419 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[NH:13][NH:14][C:15]([C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=2[F:25])=[N:16][N:17]=1>O.C(O)(=O)C>[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[N:16][C:15]([C:18]2[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=2[F:24])=[N:14][N:13]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 178505724HCID 178505724, compound

Product 1

HCID 233627443-(2-Bromophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazineYield 95.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 0.26 g of sodium nitrite in 1 ml of water is dropped to a solution containing 0.62 g of 3-(2-bromophenyl)-6-(2,6-difluorophenyl)-1,2-dihydro-1,2,4,5-tetrazine [prepared in the preceeding step c.)] in 2 ml of glacial acetic acid at room temperature under stirring. The progress of the reaction is followed by thin layer chromatography (TLC). The reddish-violet crystals are filtered, washed with water until neutral and dried to give 0.59 g of crystalline desired product, i.e. the title compound of Example 1. This crude product is recrystallized from a mixture of gasoline and acetone, m.p.: 168° C.

Workup

  1. customprepared in the preceeding step c
  2. filtrationThe reddish-violet crystals are filtered
  3. washwashed with water until neutral and
  4. customdried

Sources & evidence

ORD record
ord-0f286438188e4a2b8c243fb0727e8dc3
Source dataset
uspto-grants-1995_10
Patent number
US05455237

Reaction notes

Loading…