Ammonium Chloride → HCID 178516764, compound

HRID 1884579Notes

Reaction equation

HRID 1884579 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-6b3c0dbd45c24ce89617683663444c9a
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

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