Methyl iodide → HCID 22402970, compound

HRID 259707Notes

Reaction equation

HRID 259707 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[NH:6][C:7]2[C:8](=[CH:10][CH:11]=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:9]=1.IC.[C:24](=O)(O)[O-].[Na+]>CO.O1CCCC1.Cl>[CH3:24][N:9]1[C:8]2=[CH:10][CH:11]=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:7]2[N:6]=[C:5]1[CH3:4]

Participants

8

Reactant 4

HCID 6328Methyl iodide2×HCID 516892Sodium BicarbonateHCID 10942334Sodium Methoxide2×HCID 178497326HCID 178497326, compound

Product 1

HCID 22402970HCID 22402970, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (1.98 g, 36.6 mmol) is added to a solution of dimethyl 2-methyl-4,5-benzimidazoledicarboxylate (7.44 g, 33.3 mmol) in methanol and tetrahydrofuran. After 5 minutes, iodomethane (2.18 mL, 35.0 mmol) is added and the mixture is stirred for 24 hours at room temperature. Additional sodium methoxide (1.80 g, 33.3 mmol) and iodomethane (2.07 mL, 33.3 mmol) are added and stirring is continued for another 15 hours. The reaction mixture is concentrated in vacuo to give a residue which is dispersed in dilute hydrochloric acid, and treated with sodium bicarbonate to pH 8 and extracted with chloroform. The combined organic extracts are dried (MgSO4) and concentrated in vacuo to give a residue which is recrystallized from ethyl acetate to afford the title product as an orange solid, mp 205°-208° C.

Workup

  1. stirringstirring
  2. waitis continued for another 15 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customto give a residue which
  5. extractionextracted with chloroform
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a residue which
  9. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-87c5568e49e24b5e80dee120d035101e
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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