Methyl iodide → 3-[3-Chloro-4-(phenethyloxy)phenyl]-1,1,3-trimethylurea

HRID 1577946Notes

Reaction equation

HRID 1577946 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H].[CH3:27]I>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([N:19]([CH3:27])[C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 129420803-[3-Chloro-4-(phenethyloxy)phenyl]-1,1-dimethylureaHCID 178418361HCID 178418361, compound

Product 1

HCID 205665603-[3-Chloro-4-(phenethyloxy)phenyl]-1,1,3-trimethylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of sodium hydride (0.48 g; 0.01 mol as 50% dispersion in oil) and THF (25 ml) is prepared and maintained under a nitrogen atmosphere. Then 3-[3-chloro-4-(phenethyloxy)phenyl]-1,1-dimethylurea (3.19 g; 0.01 mol) is added to the above mixture. Hydrogen is evolved and a thick paste forms. After about 15 minutes methyl iodide (1.4 g; 0.01 mol) is added and the reaction mixture stirred for two hours at room temperature. After two hours reaction time the paste redissolves. Next, most of the THF is removed under vacuum, the residue dissolved in methylene chloride. The methylene chloride solution is washed with water, dried over sodium sulfate and evaporated to afford the title product as an oil.

Workup

  1. customis prepared
  2. temperaturemaintained under a nitrogen atmosphere
  3. customAfter two hours reaction time the paste
  4. dissolutionredissolves
  5. customNext, most of the THF is removed under vacuum
  6. dissolutionthe residue dissolved in methylene chloride
  7. washThe methylene chloride solution is washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-85a6c12f53584df7ad90440c0bf97ed4
Source dataset
uspto-grants-1981_09
Patent number
US04289903

Reaction notes

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