Iodoethane → HCID 44553561, compound

HRID 1254040Notes

Reaction equation

HRID 1254040 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](I)[CH3:31]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH2:30][CH3:31])[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178509630HCID 178509630, compound

Product 1

HCID 44553561HCID 44553561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-{5-[(4-chlorophenyl)thio]-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 2, 10 mg) in THF (1 mL) was added NaH (60% wt, 15 mg) at 0° C. After stirring for 5 min, EtI (0.05 mL) was added. The reaction was stirred at 50° C. overnight, then quenched with aq NH4Cl to adjust the pH to 6-8. The product was extracted with EtOAc and the combined extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was subject to silica column chromatography (0-15% EtOAc in hexanes) to give the title compound. LCMS: m/z 416 (M+H)+.

Workup

  1. customat 0° C
  2. stirringThe reaction was stirred at 50° C. overnight
  3. customquenched with aq NH4Cl
  4. extractionThe product was extracted with EtOAc
  5. washthe combined extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-970a83f1890442f5816b175d87774446
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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