Methyl iodide → HCID 68877760, compound

HRID 1867530Notes

Reaction equation

HRID 1867530 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][CH3:17])=[CH:12][C:11]=3[O:18][CH3:19])[CH:8]=[CH:9][C:2]=12.[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>CN(C=O)C>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([N:16]([CH3:20])[CH3:17])=[CH:12][C:11]=3[O:18][CH3:19])[CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68878052HCID 68878052, compound

Product 1

HCID 68877760HCID 68877760, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.8 mmol) of (4-benzo[1,2,5]oxadiazol-5-yl-3-methoxy-phenyl)-methyl-amine are stirred at 0 to 5° C. in 5 mL of DMF, then over 1 minute treated with 1 mL NaHMDS-solution (1.0 M, 1.25 eq.) and stirred another minute. Then, 0.5 mL (7.8 mmol, 10 eq.) of methyliodide is added and stirred 2 minutes under warming to rt. Then, the mixture is extracted with ethyl acetate/aqueous NaHCO3, the combined organic layers dried with sodium sulfate and concentrated. This yields the desired product as a reddish-yellow solid.

Workup

  1. stirringstirred 2 minutes
  2. extractionThen, the mixture is extracted with ethyl acetate/aqueous NaHCO3
  3. dry with materialthe combined organic layers dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4fd8ccea09314760a5cba908595d7fe4
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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