Methyl iodide → HCID 19016513, compound

HRID 1728607Notes

Reaction equation

HRID 1728607 reaction equation
[H-].[Na+].[CH3:3][N:4]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[CH:18]=[CH:17]2)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:6].CI.Cl[CH2:27]Cl>CN(C)C=O>[CH3:3][N:4]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[CH:18]=[CH:17]2)[C:5]([N:7]([CH3:27])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 19016517HCID 19016517, compound

Product 1

HCID 19016513HCID 19016513, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 80% sodium hydride (0.06 g; 2 mM) in dimethylformamide (5 ml), was added the monomethyl urea (E9) (0.5 g; 1.79 mM). After stirring at room temperature for 0.5 h, methyl iodide (0.12 ml; 1.93 mM) was added dropwise. Stirring was continued at room temperature for 1 h, then heated at 50° C. for 1 h. The reaction mixture was cooled in ice, then quenched with water. The mixture was then extracted with dichloromethane, washed with water, dried over sodium sulphate and evaporated to give the crude product (0.59 g). Chromatography on silica using dichloromethane as eluant afforded the title compound (0.31 g; 60%) which was recrystallised from cyclohexane to give a white solid (160 mg) m.p. 91°-92.5° C.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 1 h
  3. temperatureheated at 50° C. for 1 h
  4. temperatureThe reaction mixture was cooled in ice
  5. customquenched with water
  6. extractionThe mixture was then extracted with dichloromethane
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customto give the crude product (0.59 g)

Sources & evidence

ORD record
ord-059485cd0bce473d992af2fe84497d83
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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