Ammonium Chloride → HCID 178505729, compound

HRID 251549Notes

Reaction equation

HRID 251549 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[NH4+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]2[NH:22][N:21]=[N:20][N:14]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21964471(4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile

Product 1

HCID 178505729HCID 178505729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile (Step A, 5 g, 19.3 mmol), NaN3 (1.3 g, 20 mmol), and NH4Cl (1.06 g, 20 mmol) in dry DMF (60 ml) was heated at 90° C. for 16 hours. The solvent was removed in vacuo and the oily residue was partitioned between EtOAc and water (acidified to pH 1 with conc. HCl). The organic layer was washed with water, dried over Na2SO4, filtered and concentrated to a brown semisolid. The purification was done by flash chromatography on silica gel column (chloroform:methanol, 9:1) to provide the title compound as a light creamy solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe oily residue was partitioned between EtOAc and water (acidified to pH 1 with conc. HCl)
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a brown semisolid
  7. customThe purification

Sources & evidence

ORD record
ord-87529f554c0b48ca9bbbccddadc34398
Source dataset
uspto-grants-2011_01
Patent number
US07863475B2

Reaction notes

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