N-Iodosuccinimide → HCID 68857380, compound

HRID 226020Notes

Reaction equation

HRID 226020 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]([CH3:10])[CH:8]=[N:9][C:5]=2[CH:4]=1.C([Li])(C)(C)C.C1C(=O)N([I:25])C(=O)C1>C1COCC1>[I:25][C:8]1[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:9]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 42927805-Methoxy-1-methylbenzimidazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 68857380HCID 68857380, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 0.500 g (1.75 mmol) of 5-methoxy-1-methylbenzimidazole in 10 mL of dry THF is cooled to −78° C. 2.47 mL (4.20 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at −78° C. for 1 h. 0.472 g (2.1 mmol) of NIS in 10 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3×50 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.125 g of the title compound, 25% yield. MS, ES+=289.0 (M+1); 1H NMR (DMSO-d6) δ 7.439-7.417 (d, 1H); 7.147-7.141 (m, 1H); 6.771-6.743 (m, 1H); 3.794 (s, 3H); 3.707 (s, 3H) ppm.

Workup

  1. customReaction
  2. customis removed from bath
  3. stirringstirred at room temperature for 1 hour
  4. customquenched with saturated aqueous solution of ammonium chloride
  5. additiondiluted with dichloromethane
  6. customThe layers are separated
  7. extractionthe aqueous is extracted 3×50 mL dichloromethane
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe crude mixture is purified by chromatography
  11. additionThe product containing fractions

Sources & evidence

ORD record
ord-4695e8f359e6428bb4db0bb0936cddef
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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