Benzyl Chloride → HCID 20136108, compound

HRID 579704Notes

Reaction equation

HRID 579704 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([CH3:7])[C:4](=[O:8])[N:3]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18])=[C:11]([CH3:22])[CH:10]=1.[H-].[Na+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:25]([O:1][CH:2]1[CH2:6][N:5]([CH3:7])[C:4](=[O:8])[N:3]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:21])([F:20])[CH:17]([F:18])[F:19])=[C:11]([CH3:22])[CH:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 20136111HCID 20136111, compound

Product 1

HCID 20136108HCID 20136108, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

16.1 g (0.05 mol) of 4-hydroxy-1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidin-2-one are dissolved in 150 ml of acetonitrile, and 1.50 g of sodium hydride (80% strength in white oil) are added at 5° C. The mixture is stirred for 10 minutes at 5° C., and 6.40 g (0.05 mol) of benzyl chloride are subsequently added dropwise at 5° C. The mixture is stirred for 5 hours at 50°and poured into 400 ml of ice-water. The mixture is extracted twice with 100 ml of methylene chloride in each case, and the combined methylene chloride phases are washed with 100 ml of water and dried over sodium sulfate. After removing the solvent by distillation, 19.4 g (94% of theory) of 4-benzyloxy-1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidin-2-one are obtained in the form of a pale yellow oil.

Workup

  1. stirringThe mixture is stirred for 5 hours at 50°and
  2. extractionThe mixture is extracted twice with 100 ml of methylene chloride in each case
  3. washthe combined methylene chloride phases are washed with 100 ml of water
  4. dry with materialdried over sodium sulfate
  5. customAfter removing the solvent
  6. distillationby distillation, 19.4 g (94% of theory) of 4-benzyloxy-1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidin-2-one
  7. customare obtained in the form of a pale yellow oil

Sources & evidence

ORD record
ord-33a281bcfbca4ff1a2a0f69e443ebaf0
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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