Pyridinium chloride → HCID 70654380, compound

HRID 539449Notes

Reaction equation

HRID 539449 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=[C:8]([CH:23]([CH3:25])[CH3:24])[C:9]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=1)([CH3:3])[CH3:2].Cl.N1C=CC=CC=1>>[CH:23]([C:8]1[CH:7]=[C:6]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 70654740HCID 70654740, compound

Product 1

HCID 70654380HCID 70654380, compoundYield 95.2%

Conditions

Temperature
200 °C

Procedure

A mixture of 1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(3-methoxyphenyl)-1H-imidazole (5.57 g, 13.57 mmol) and pyridine hydrochloride (9.41 g, 81 mmol) were fused with stirring at 200° C. for 13 h. After the reaction was complete, the mixture was partitioned between water and AcOEt. AcOEt layer was separated, washed with water (3×) and brine, and then purified by silica gel column chromatography using DCM/MeOH (96/4) as eluant to afford an off-white solid (5.12 g, 95%).

Workup

  1. customthe mixture was partitioned between water and AcOEt
  2. customAcOEt layer was separated
  3. washwashed with water (3×) and brine
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-29823f4bc3794a139e3772c50bbaebfa
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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