Sodium borohydride → 3-(3,4-Dichlorophenyl)-4-hydroxy-1-methylimidazolidin-2-one

HRID 483050Notes

Reaction equation

HRID 483050 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[C:3]1=[O:4].[BH4-].[Na+]>CO>[CH3:1][N:2]1[CH2:8][CH:6]([OH:7])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 130655013-(3,4-Dichlorophenyl)-1-methylimidazolidine-2,4-dione

Product 1

HCID 133423223-(3,4-Dichlorophenyl)-4-hydroxy-1-methylimidazolidin-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A 10.4 g (0.04 mole) quantity of 1-methyl-3-(3,4-dichlorophenyl)hydantoin was suspended in 80 ml of methanol. The suspension was cooled to 10° C. and 1.5 g of sodium borohydride was added thereto with stirring. After the addition, the mixture was stirred for 30 minutes and warmed to room temperature, followed by further agitation for 2 hours. After completion of the reaction, the reaction mixture was concentrated and water was added to the residue to deposit crystals. The crystals were filtered and recrystallized from ethanol, affording 9.2 g of white crystals in 88% yield.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred for 30 minutes
  3. temperaturewarmed to room temperature
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated
  6. additionwater was added to the residue to deposit crystals
  7. filtrationThe crystals were filtered
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ee842a301c4c485abcff6b956cd87ed3
Source dataset
uspto-grants-1986_03
Patent number
US04578107

Reaction notes

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