Ammonium Chloride → HCID 178516764, compound

HRID 1267958Notes

Reaction equation

HRID 1267958 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[O:6][C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[OH:23])=[CH:11][CH:10]=[CH:9][N:8]=1)#[N:2].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:27]1[C:1]([C:3]2[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=2)[O:6][C:7]2[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[OH:23])=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:2][N:29]=[N:28]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23506248HCID 23506248, compound

Product 1

HCID 178516764HCID 178516764, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2-(3-Cyanophenoxy)-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine (0.85 g, 2.5 mmol) obtained in Example 28 is dissolved in DMF (10 ml), and thereto are added sodium azide (0.20 g, 3.0 mmol) and ammonium chloride (0.16 g, 3.0 mmol). The mixture is stirred at 130° C. for one hour, and the reaction solution is concentrated under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent: acetic acid/ethanol), and recrystallized from ethanol to give the title compound (0.31 g) as pale brown crystals, m.p. 220-240° C. (decomposed).

Workup

  1. concentrationthe reaction solution is concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customis purified by silica gel column chromatography (eluent: acetic acid/ethanol)
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8f1501ef0e0d4962a4aee88b094839cd
Source dataset
uspto-grants-2003_04
Patent number
US06555557B1

Reaction notes

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