Methyl iodide → HCID 22402957, compound

HRID 439735Notes

Reaction equation

HRID 439735 reaction equation
[NH:1]1[C:5]2=[CH:6][CH:7]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:4]2[N:3]=[N:2]1.[H-].[Na+].I[CH3:21]>CN(C)C=O>[CH3:21][N:1]1[C:5]2=[CH:6][CH:7]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:4]2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178497400HCID 178497400, compound

Product 1

HCID 22402957HCID 22402957, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of dimethyl 1H-benzotriazole-4,5-dicarboxylate (10.1 g, 43 mmol) in dimethylformamide is treated portion-wise, with cooling, with sodium hydride. When gas evolution has ceased, the reaction mixture is treated dropwise with iodomethane (6.7 g, 46 mmol) stirred at room temperature for 2 hours, concentrated in vacuo and diluted with a mixture of chloroform and water. The layers are separated; the organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and 35% ethyl acetate in hexanes to give the title product as a white solid, 3.15 g, mp 146°-147° C. The structure is determined by NMR NOE experiments.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with a mixture of chloroform and water
  3. customThe layers are separated
  4. washthe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is chromatographed

Sources & evidence

ORD record
ord-d5950975abc94b2a924634507dae0464
Source dataset
uspto-grants-1996_05
Patent number
US05516751

Reaction notes

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