Sodium borohydride → HCID 20136111, compound

HRID 579701Notes

Reaction equation

HRID 579701 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:20])([F:19])[CH:16]([F:18])[F:17])=[C:10]([CH3:21])[CH:9]=2)[C:3]1=[O:22].[BH4-].[Na+]>C(O)(C)C>[OH:7][CH:5]1[CH2:6][N:2]([CH3:1])[C:3](=[O:22])[N:4]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:20])([F:19])[CH:16]([F:17])[F:18])=[C:10]([CH3:21])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20136115HCID 20136115, compound

Product 1

HCID 20136111HCID 20136111, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

16.0 g (0.05 mol) of 1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidine-2,4-dione are dissolved in 100 ml of isopropanol, and 2.85 g (0.075 mol) of sodium borohydride are added at a rate such that the temperature increases to 40° C. After the addition is complete, the mixture is stirred for a further 30 minutes at 40° C., and poured into 300 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, 15.4 g (96% of theory) of 4-hydroxy-1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidin-2-one are obtained in the form of a pale yellow viscous oil.

Workup

  1. additionAfter the addition
  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, 15.4 g (96% of theory) of 4-hydroxy-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 viscous oil

Sources & evidence

ORD record
ord-20d0a26371ee40f196fd2cd70dcd438e
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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