Methyl iodide → HCID 58742996, compound

HRID 722407Notes

Reaction equation

HRID 722407 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:20])[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 3598338ST50554379

Product 1

HCID 58742996HCID 58742996, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclohexanecarboxylic acid (4-fluoro-3-nitro-phenyl)amide (see Example 1) (0.75 g, 2.82 mmol) in DMSO (15 mL) was added a 1M solution of sodium bistrimethylsilylamide (3.36 mL, 3.36 mmol), with stirring at room temperature. After 15 min, iodomethane (0.53 mL, 8.5 mmol) was added. After 1 h, the mixture was diluted with ethyl acetate, washed twice with water, dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography, eluting with hexane/ethyl acetate (7:3) to give cyclohexanecarboxylic acid (4-fluoro-3-nitro-phenyl)-methyl-amide (402 mg, 51%) as the first eluted component.

Workup

  1. waitAfter 1 h
  2. washwashed twice with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-fd910d1b33b04ef3b3489de7d069da3c
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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