Ethanolamine → 3-n-Butyl-5-(thiophen-2-yl methylene) hydantoin

HRID 847729Notes

Reaction equation

HRID 847729 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH2:8]([N:12]1[C:16](=[O:17])[CH2:15][NH:14][C:13]1=[O:18])[CH2:9][CH2:10][CH3:11].C(CN)O>O.C(O)C>[CH2:8]([N:12]1[C:16](=[O:17])[C:15](=[CH:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[NH:14][C:13]1=[O:18])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 73642-ThiophenecarboxaldehydeHCID 5682353-Butylimidazolidine-2,4-dione

Product 1

HCID 541167003-n-Butyl-5-(thiophen-2-yl methylene) hydantoinYield 51.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of thiophene-2-carboxaldehyde (5.6 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 4 hours. The mixture was cooled in the refrigerator and the resultant brownish yellow crystals filtered off, washed with water, sucked dry and recrystallised from ethyl acetate (with carbon treatment) to give the title compound (6.4 g; 51%) having m.p. 140° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture was cooled in the refrigerator
  3. filtrationthe resultant brownish yellow crystals filtered off
  4. washwashed with water
  5. customsucked dry
  6. customrecrystallised from ethyl acetate (with carbon treatment)

Sources & evidence

ORD record
ord-6702625bc23d4655ae427b9f26a2a1c2
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

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