Chlorosuccinimide → 2-(4-chloro-5-phenyl-1H-imidazol-1-yl)-5-(methylsulfonyl)pyridine

HRID 1523270Notes

Reaction equation

HRID 1523270 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:13]=[CH:12]2)=[N:9][CH:10]=1)(=[O:4])=[O:3].[Cl:22]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:22][C:14]1[N:13]=[CH:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][N:9]=2)[C:15]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 680162165-(methylsulfonyl)-2-(5-phenyl-1H-imidazol-1-yl)pyridine

Product 1

HCID 680162152-(4-chloro-5-phenyl-1H-imidazol-1-yl)-5-(methylsulfonyl)pyridineYield 30%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

5-(methylsulfonyl)-2-(5-phenyl-1H-imidazol-1-yl)pyridine (50 g), N-chlorosuccinimide (20 g) and azo-bis-isobutyronitrile (500 mg) were dissolved in 3 L tetrachloromethane to allow reflux overnight. The reaction mixture was cooled to room temperature, and the residual solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain the target compound (15 g). 1H-NMR (300 MHz, CDCl3): δ 3.12 (3H, s), 6.78 (1H, dd), 7.28 (2H, m), 7.44 (3H, m), 8.06 (1H, dd), 8.25 (1H, s), 9.03 (1H, dd); LC-MS m/z: 335 [M++1], purity (HPLC)>95%.

Workup

  1. temperatureto allow reflux overnight
  2. customthe residual solvent was removed under reduced pressure
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-54dc92d7a4354e5ab3d588533c74cfa5
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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