Ammonium Chloride → HCID 178420729, compound

HRID 1180686Notes

Reaction equation

HRID 1180686 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][C:2]=1[C:15]#[N:16].[NH4+].[Cl-].[N-:19]=[N+:20]=[N-:21].[Na+]>[Li+].[Cl-].CN(C=O)C>[NH:19]1[C:15]([C:2]2[CH:3]=[CH:4][C:5]3[C:14](=[C:13]4[C:8](=[CH:7][CH:6]=3)[CH:9]=[CH:10][CH:11]=[N:12]4)[N:1]=2)=[N:16][N:21]=[N:20]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 6803411,10-Phenanthroline-2-carbonitrile

Product 1

HCID 178420729HCID 178420729, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 433294Lithium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a flask was added a mixture of 6 g [1,10]phenanthroline-2-carbonitrile, 3.1 g NH4Cl, 3.8 g NaN3, 0.01 g LiCl and 60 ml DMF, and the mixture was then heated to 120-130° C. and stirred overnight. After completion of reaction, the reaction mixture was cooled to room temperature, filtered to remove solids, and vacuum distallated to remove DMF, and then 300 ml water was added. Next, HCl(aq) was added to adjust pH value to about 4, and stirred for 30 minutes. Finally, the solution was filtered to give solids, and then the solids were washed by water and dried to obtain products 2-(1H-tetrazol-5-yl)-[1,10]phenanthroline 6.1 g. (yield=84.0%).

Workup

  1. additionTo a flask was added
  2. customAfter completion of reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customto remove solids, and vacuum
  6. customto remove DMF
  7. addition300 ml water was added
  8. additionNext, HCl(aq) was added
  9. stirringstirred for 30 minutes
  10. filtrationFinally, the solution was filtered
  11. customto give solids
  12. washthe solids were washed by water
  13. customdried

Sources & evidence

ORD record
ord-aef9b00296c6400999ffa43cc0edf22a
Source dataset
uspto-grants-2007_10
Patent number
US07282586B1

Reaction notes

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