Ammonium Chloride → HCID 178424787, compound

HRID 337243Notes

Reaction equation

HRID 337243 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:9]2[NH:21][N:20]=[N:19][N:10]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66959094HCID 66959094, compound

Product 1

HCID 178424787HCID 178424787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(2,6-Dimethylbenzyloxy)benzonitrile (Step A, 3 g, 11.8 mmol), sodium azide (0.847 g, 13 mmol) and ammonium chloride (0.697 g, 13 mmol) in dry dimethylformamide (30 ml) was heated under argon at 110° C. for 14 hours or until all the starting material is consumed. Water was added to the reaction mixture to dissolve all the solids; the solution was taken in brine and extracted with ethyl acetate (2×). The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 95:5) to give the title compound as a white solid.

Workup

  1. customis consumed
  2. additionWater was added to the reaction mixture
  3. dissolutionto dissolve all the solids
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5)

Sources & evidence

ORD record
ord-6d758ba44836493e9679b1f8ae4ee748
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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