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

HRID 1733314Notes

Reaction equation

HRID 1733314 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-b4c87ca10bb143e5881e04006a33f1b5
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

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