Ammonium Chloride → HCID 21180769, compound

HRID 1386718Notes

Reaction equation

HRID 1386718 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:3]2[N:9]=[N:10][N:11]=[C:4]2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 693532,5-Dibromopyridine

Product 1

HCID 21180769HCID 21180769, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,5-Dibromopyridine (1.0 g, 4.2 mmol), sodium azide (412 mg, 6.3 mmol) and NH4Cl (339 mg, 6.3 mmol) were heated in 20 mL DMF to 100° C. for 16 h. The mixture was diluted with 150 mL EtOAc, washed with H2O (2×) and sat'd NaCl then dried over Na2SO4 and concentrated. Flash chromatography (30 g silica, 2/1 hexane/EtOAc eluant) afforded 212 mg (25%) of the title compound.

Workup

  1. washwashed with H2O (2×)
  2. dry with materialthen dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-88033538c181421e9fbea7e71a3c2890
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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