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

HRID 1733305Notes

Reaction equation

HRID 1733305 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=O.[CH2:15]([N:19]1[C:23](=[O:24])[CH2:22][NH:21][C:20]1=[O:25])[CH2:16][CH2:17][CH3:18].C(CN)O>O.C(O)C>[CH2:15]([N:19]1[C:23](=[O:24])[C:22](=[CH:5][C:4]2[CH:7]=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[CH:10][C:3]=2[O:2][CH3:1])[NH:21][C:20]1=[O:25])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 205252,4,5-TrimethoxybenzaldehydeHCID 5682353-Butylimidazolidine-2,4-dione

Product 1

HCID 539642823-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoinYield 87%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 2,4,5-trimethoxybenzaldehyde (9.8 g; 0.05 mole), 3-n-butylhydantoin (7.8 g: 0.05 mole) and ethanolamine (4.6 g; 0.075 mole) in water/ethanol (50 ml/30 ml) was stirred and boiled under reflux for 3 hours. The cloudy solution was cooled in the refrigerator and the resultant yellow solid filtered off, washed with water, sucked dry and recrystallised from ethanol to give the title compound (14.5 g; 87%) m.p. 170° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe cloudy solution was cooled in the refrigerator
  3. filtrationthe resultant yellow solid filtered off
  4. washwashed with water
  5. customsucked dry
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-f2440fb1652240d8b34ed477f0e58202
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

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