3-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoin → 3-n-Butyl-5-(2,4,5-trimethoxybenzyl) hydantoin

HRID 847724Notes

Reaction equation

HRID 847724 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](=[CH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[O:22][CH3:23])[NH:7][C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]>[Pd].C(O)(=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[O:22][CH3:23])[NH:7][C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 539642823-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoin

Product 1

HCID 127907223-n-Butyl-5-(2,4,5-trimethoxybenzyl) hydantoin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoin (10.0 g; 0.03 mole) was mixed with glacial acetic acid (150 ml.) and hydrogenated in a Parr apparatus in the presence of 5% Pd/C (2 g). After 2 hours the catalyst was filtered off, washed with warm acetic acid and the colourless filtrate evaporated in vacuo to give a white crystalline solid. Recrystallisation from ethyl acetate gave the title compound, yield 9.2 g (91% ), m.p. 122° C.

Workup

  1. filtrationAfter 2 hours the catalyst was filtered off
  2. washwashed with warm acetic acid
  3. customthe colourless filtrate evaporated in vacuo
  4. customto give a white crystalline solid
  5. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-ce3a288b229b4defa7c5dbe1380b8974
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

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