Hydrochloric Acid → (RS)-5-[[3-Methoxy-2-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedione

HRID 260074

Reaction equation

HRID 260074 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([CH:9]=[C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH:6]=[CH:7][CH:8]=1.Cl.C(=C1NC(=O)NC1=O)C1C=CC=CC=1>CO.[Zn]>[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([CH2:9][CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 978575-BenzylidenehydantoinHCID 542510915-[[3-Methoxy-2-(phenylmethoxy)phenyl]methylene]-2,4-imidazolidinedione

Product 1

HCID 15296728(RS)-5-[[3-Methoxy-2-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedioneYield 47.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Zinc powder (40.00 g; 0.61 mole) is added to a stirred suspension of 48.00 g (0.16 mole) of the benzylidine hydantoin from Example 3 in 1,200 mL of methanol under nitrogen. Concentrated hydrochloric acid (30 mL) is added and the mixture is heated on the steam bath for 20 minutes (after 10 minutes the starting benzylidene hydantoin dissolves). Another 30 mL of concentrated hydrochloric acid is added and the mixture is heated at reflux for another 20 minutes. The cooled (50° C.) mixture is cautiously filtered and the cake washed with 100 mL of methanol. Water (500 mL) is added to the filtrate to yield 24.60 g of crystalline product; mp 202°-204° C.

Workup

  1. dissolutiondissolves)
  2. temperaturethe mixture is heated
  3. temperatureat reflux for another 20 minutes
  4. filtrationis cautiously filtered
  5. washthe cake washed with 100 mL of methanol
  6. additionWater (500 mL) is added to the filtrate

Sources & evidence

ORD record
ord-edf479c62b5844d892dc201bc6071dd9
Source dataset
uspto-grants-1996_06
Patent number
US05525614

Linked notes

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