Methyl iodide → HCID 15767244, compound

HRID 1421379Notes

Reaction equation

HRID 1421379 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:10](=[O:13])[CH2:11][CH3:12])[OH:9].[H-].[Na+].[CH3:16]I>CN(C)C=O.O>[CH3:16][O:9][N:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:10](=[O:13])[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15767243HCID 15767243, compound

Product 1

HCID 15767244HCID 15767244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

At 25 to 30° C., a solution of 22.7 g (0.127 mol) (Example 6a) of N-(2-methylphenyl)-N-propionyl-hydroxylamine in 50 ml of dimethylformamide is dripped into a stirred mixture of 3.4 g (0.14 mol) of NaH in 150 ml of dimethylformamide. After completion of gas evolution (15 mins) 18.4 g (0.13 mol) of methyl iodide is added and the mixture is stirred overnight at room temperature. The reaction mixture is then diluted with water and the aqueous phase is extracted three times with methyl tert-butyl ether. The combined organic phases are extracted with water, dried over MgSO4 and evaporated down. The residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate. There is obtained 18 g (0.081 mol=64%) of the title compound as a yellow oil.

Workup

  1. extractionthe aqueous phase is extracted three times with methyl tert-butyl ether
  2. extractionThe combined organic phases are extracted with water
  3. dry with materialdried over MgSO4
  4. customevaporated down
  5. customThe residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-7eeafada3e094f8e87d20a44f83b8f98
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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