Ammonium Chloride → HCID 10182766, compound

HRID 2305958Notes

Reaction equation

HRID 2305958 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]([S:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:20])=[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[N:27]=[N:28][NH:29][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]([S:18]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)(=[O:20])=[O:19])[CH:12]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18433405HCID 18433405, compound

Product 1

HCID 10182766HCID 10182766, compound

Conditions

Temperature
143 °C

Procedure

4-[2,6-Dichloro-4-(2H-tetrazol-5-yl)-phenoxy]-2-(pyrrolidine-1-sulfonyl)-phenol was prepared from 3,5-dichloro-4-[4-hydroxy-3-(pyrrolidine-1-sulfonyl)-phenoxy]-benzonitrile according to a procedure analogous to that described in EXAMPLE 1, Step C. Sodium azide (4.0 equiv) and ammonium chloride (4.0 equiv) were used, and the reaction was heated to 143° C. for 40 hours. After the reaction had been acidified and the crude product collected by filtration, the solid was dissolved in MeOH, filtered, and the filtrate was concentrated. The residue was purified by preparative TLC (methanol:water:chloroform=19:1:47) to afford the title product of Example 2. MS (APCI−) Calc.: 455.0, Found: 454.2 (M−1).

Workup

  1. filtrationthe crude product collected by filtration
  2. dissolutionthe solid was dissolved in MeOH
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by preparative TLC (methanol:water:chloroform=19:1:47)

Sources & evidence

ORD record
ord-c5f6e0a225224498afdba33a3993dadc
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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