Iodoethane → HCID 22402939, compound

HRID 259716Notes

Reaction equation

HRID 259716 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14]2=[CH:15][CH:16]=[C:17]([C:23]([O:25][CH3:26])=[O:24])[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:13]2[N:12]=[C:11]1[CH3:27])[C:4]1C=CC=CC=1.[H][H].C(I)C>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([N:10]1[C:14]2=[CH:15][CH:16]=[C:17]([C:23]([O:25][CH3:26])=[O:24])[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:13]2[N:12]=[C:11]1[CH3:27])[CH3:4]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22402944HCID 22402944, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22402939HCID 22402939, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (1.38 g, 46.0 mmol, 80% oil dispersion) is added in portions to a solution of dimethyl 1-benzyl-2-methyl-4,5-benzimidazoledicarboxylate (10.9 g, 43.8 mmol) in dry dimethylformamide at 0° C. After evolution of hydrogen ceases, ethyl iodide (3.68 mL, 46.1 mmol) is added. The reaction mixture is stirred at room temperature overnight, treated with ethyl acetate, and filtered. The filtrate is concentrated in vacuo; the resultant residue is recrystallized from 50% ethyl acetate:hexanes to yield the title product as a light yellow powder (3.84 g, 31.7%), mp 126.5°-128° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customthe resultant residue is recrystallized from 50% ethyl acetate

Sources & evidence

ORD record
ord-79f89fed3b894d77b935ae8b5f886d6f
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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