Chloromethyl ethyl ether → HCID 19896198, compound

HRID 1196777Notes

Reaction equation

HRID 1196777 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[NH:12][C:11]1=[O:21].[H-].[Na+].Cl[CH2:25][O:26][CH2:27][CH3:28]>O1CCCC1>[CH2:27]([O:26][CH2:25][N:12]1[C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][C:15](=[O:16])[N:10]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=2[Cl:9])[C:11]1=[O:21])[CH3:28]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride2×HCID 19896218HCID 19896218, compound

Product 1

HCID 19896198HCID 19896198, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.50 g of 3-(2,4,6-trichlorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was added to a 10 ml tetrahydrofuran solution of 0.30 g of sodium hydride (purity: 55%) with stirring under ice cooling, and the mixed solution was stirred at room temperature for 15 minutes. Then, after adding 0.70 g of chloromethylethyl ether, the solution was further stirred at room temperature for 3 hours. Then ice was added to the solution to decompose excess sodium hydride. The resulting mixture was extracted with 100 ml of ethyl acetate, and the obtained organic layer was washed thrice with water and dried over magnesium sulfate. Then the solvent was distilled away under reduced pressure to obtain 1.2 g of the objective compound as a viscous oily substance.

Workup

  1. stirringthe mixed solution was stirred at room temperature for 15 minutes
  2. stirringthe solution was further stirred at room temperature for 3 hours
  3. additionThen ice was added to the solution
  4. extractionThe resulting mixture was extracted with 100 ml of ethyl acetate
  5. washthe obtained organic layer was washed thrice with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThen the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-10ca0ab487984bc78723c02887dd5083
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

Loading…