Ammonium Chloride → HCID 178497694, compound

HRID 1873588Notes

Reaction equation

HRID 1873588 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].[N-:13]=[N+:14]=[N-:15].[Na+].[Cl-].[NH4+].N([O-])=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[NH:13]1[C:1]([C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[N:2][N:15]=[N:14]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 83554Benzoic acid, 3-cyano-, methyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 178497694HCID 178497694, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1.00 g (6.21 mmol) of the compound from Example 47A are initially charged in 18 ml of dry DMF. 2.42 g (37.23 mmol) of sodium azide and 1.99 g (37.23 mmol) of ammonium chloride are then added. The reaction mixture is stirred at 120° C. for 2.5 h. After cooling to RT the mixture is poured into a mixture of 30 ml of ice-water and 10 ml of ethyl acetate. 2.57 g (37.23 mmol) of sodium nitrite are added to this mixture to destroy excess azide. By addition of 6 N hydrochloric acid, the pH is then adjusted to 1-2 and the mixture is stirred at RT for 30 min. The mixture is extracted three times with in each case 20 ml of a 1:1 mixture of ethyl acetate and THF. The precipitate formed is filtered off with suction and dried under reduced pressure. In order to isolate more product, the separated organic phase is washed in each case once with in each case 10 ml of water and saturated aqueous sodium chloride solution. After drying over magnesium sulfate the solvent is removed on a rotary evaporator. Both solids are combined and used for the next step.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. customto destroy excess azide
  3. additionBy addition of 6 N hydrochloric acid
  4. stirringthe mixture is stirred at RT for 30 min
  5. extractionThe mixture is extracted three times
  6. additionwith in each case 20 ml of a 1:1 mixture of ethyl acetate and THF
  7. customThe precipitate formed
  8. filtrationis filtered off with suction
  9. customdried under reduced pressure
  10. customIn order to isolate more product
  11. washthe separated organic phase is washed in each case once with in each case 10 ml of water and saturated aqueous sodium chloride solution
  12. dry with materialAfter drying over magnesium sulfate the solvent
  13. customis removed on a rotary evaporator

Sources & evidence

ORD record
ord-0ef22cf5d38a4564917ed29acd3875e4
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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