Ammonium Chloride → HCID 178507761, compound

HRID 1993561Notes

Reaction equation

HRID 1993561 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]#[N:14])[CH:8]=2)=[CH:4][CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:17]1[C:13]([C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:15]=[CH:16][C:2]([NH2:1])=[CH:3][CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[N:14][N:19]=[N:18]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 53399142HCID 53399142, compound

Product 1

HCID 178507761HCID 178507761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(4-amino-phenoxy)-pyridine-2-carbonitrile (Example 102) (2.6 g, 12.3 mmol), sodium azide (6.6 g, 102 mmol, 8.3 equiv), and ammonium chloride in DMF abs. (180 mL) is heated to 70° C. for 7.5 h, under an argon atmosphere. The reaction mixture is allowed to cool to rt, filtered through a glass sintered funnel and concentrated in vacuo. The residue is purified by silica gel (390 g) column chromatography (CH2Cl2/MeOH, 80/20) to afford the title compound as a beige solid: ES-MS: 255.0 [M+H]+; single peak at tR=3.98 min (System 2); Rf=0.20 (CH2Cl2/MeOH, 75/25).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered through a glass sintered funnel
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel (390 g) column chromatography (CH2Cl2/MeOH, 80/20)

Sources & evidence

ORD record
ord-6a917474ccb64ec39931f9617366f377
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…