Sodium borohydride → HCID 20136105, compound

HRID 579700Notes

Reaction equation

HRID 579700 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[CH2:13][N:12]([CH3:16])[C:11]2=[O:17])=[C:4]([F:18])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[CH:14]([OH:15])[CH2:13][N:12]([CH3:16])[C:11]2=[O:17])=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20136109HCID 20136109, compound

Product 1

HCID 20136105HCID 20136105, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

27.3 g (0.10 mol) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-imidazolidine-2,4-dione are dissolved in 200 ml of methanol, and 5.7 g (0.15 mol) of sodium borohydride are added in portions at a rate such that the temperature increases to 30°-35° C. When the addition is complete, the mixture is stirred for a further 1 hour at 30° C. The mixture is poured into 500 ml of ice-water, and the precipitate which deposits is filtered off under suction. After drying, 25.2 g (92% of theory) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-hydroxy-1-methylimidazolidin-2-one are obtained in the form of colorless crystals having the melting point 138°-140° C.

Workup

  1. temperatureincreases to 30°-35° C
  2. additionWhen the addition
  3. filtrationthe precipitate which deposits is filtered off under suction
  4. customAfter drying

Sources & evidence

ORD record
ord-4d7fa6464dc24b6494da53903df14db3
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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