Ammonium Chloride → HCID 178519769, compound

HRID 2305960Notes

Reaction equation

HRID 2305960 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:26])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH:12]=1)[C:5]#[N:6].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>>[Cl:26][C:8]1[CH:7]=[C:4]([C:5]2[NH:29][N:28]=[N:27][N:6]=2)[CH:3]=[C:2]([Cl:1])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH:12]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 18433431HCID 18433431, compound

Product 1

HCID 178519769HCID 178519769, compound

Procedure

{5-[2,6-Dichloro-4-(1H-tetrazol-5-yl)-phenoxy]-2-hydroxy-phenyl}-piperidin-1-yl-methanone was prepared from 3,5-dichloro-4-[4-hydroxy-3-(piperidine-1-carbonyl)-phenoxy]-benzonitrile according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (2.0 equiv) and ammonium chloride (2.0 equiv) were used initially, and the reaction mixture was heated to reflux for 2 hours, after which additional sodium azide (2.0 equiv) was added, and the reaction was heated to reflux for 20 hours. After the reaction had been acidified and the crude product collected by filtration, then purified by preparative TLC (methanol:water:dichloromethane 20:3:77) to afford the title product of Example 3. MS (APCI+) Calc.: 433.0, Found: 434.1 (M+1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 20 hours
  5. filtrationthe crude product collected by filtration
  6. custompurified by preparative TLC (methanol:water:dichloromethane 20:3:77)

Sources & evidence

ORD record
ord-04b9bf7c33ff4d18a6c00ca5ad6b0cf3
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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