Hydrochloric Acid → HCID 66744318, compound

HRID 535227Notes

Reaction equation

HRID 535227 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:23]=[CH:22][CH:21]=[C:18]([C:19]4[N:24]=[N:25][NH:26][N:20]=4)[CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 58131159HCID 58131159, compound

Product 1

HCID 66744318HCID 66744318, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 250 ml two-neck flask, 80 ml of N,N-dimethyl formamide (DMF), 2.92 g (6.85 mmol) of 3-(3,6-dibromo-9H-carbazol-9-yl) benzonitrile, 0.98 g (15.08 mmol) of sodium azide (NaN3), 0.81 g (15.08 mmol) of ammonium chloride (NH4Cl), and a stir bar were added. The reaction was carried out with reflux under a nitrogen atmosphere for 24 hours. After the completion of reaction, 20 ml of 10% hydrochloric acid (HCl) was added and a filtering was conducted. The crude product was purified by column chromatography to obtain 3.21 g of a white solid product of 3,6-dibromo-9-(3-2H-tetraazol-5-yl-phenyl)-9H-carbazole (yield: 82.9%).

Workup

  1. temperaturewith reflux under a nitrogen atmosphere for 24 hours
  2. additionwas added
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3b087146077d45ed8eba5f0bd47cdd1d
Source dataset
uspto-grants-2014_10
Patent number
US08859113B2

Reaction notes

Loading…