Chlorosuccinimide → HCID 57333935, compound

HRID 1523274Notes

Reaction equation

HRID 1523274 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][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)=[CH:7][N:6]=1)(=[O:4])=[O:3].[Cl:22]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.O1CCCC1>[Cl:22][C:14]1[N:13]=[CH:12][N:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:6][CH:7]=2)[C:15]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 89765606HCID 89765606, compound

Product 1

HCID 57333935HCID 57333935, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(methylsulfonyl)-5-(5-phenyl-1H-imidazol-1-yl)pyridine (83 mg, 0.28 mmol), N-chlorosuccinimide (39 mg, 0.29 mmol), azobisisobutyronitrile (2 mg) and tetrahydrofuran (10 mL) were added into a 25 mL round bottom flask, and stirred to conduct reflux reaction for 18 hours. After the reaction, the solution was concentrated under reduced pressure, and the crude product was purified by column chromatography (petroleum ether/ethyl acetate=20:1) to yield white solid target compound (56 mg, 0.17 mmol). 1H-NMR (300 MHz, CDCl3): δ 3.26 (3H, s), 7.19-7.22 (2H, m), 7.38-7.40 (3H, m), 7.66 (1H, dd), 7.71 (1H, s), 8.11 (1H, dd), 8.58 (1H, dd); LC-MS m/z: 335 [M++1]; purity (HPLC)>95%.

Workup

  1. temperatureto conduct reflux
  2. customreaction for 18 hours
  3. customAfter the reaction
  4. concentrationthe solution was concentrated under reduced pressure
  5. customthe crude product was purified by column chromatography (petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-10172325cae04742974b7fe8716f8bca
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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