Ethanolamine → 5-[(3,4-Dihydroxyphenyl)methylidene]imidazolidine-2,4-dione

HRID 597371Notes

Reaction equation

HRID 597371 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[NH:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[O:13].C(CN)O>O>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[C:17]1[NH:11][C:12](=[O:13])[NH:14][C:15]1=[O:16]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 87683,4-DihydroxybenzaldehydeHCID 10006Hydantoin

Product 1

HCID 536913815-[(3,4-Dihydroxyphenyl)methylidene]imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dihydroxybenzaldehyde (2.072 g.) and hydantoin (1.50 g.) in water (15 ml) was heated to 70° to give a clear solution. To this was added monoethanolamine (1.38 g.) and the magnetically stirred mixture was heated (90°-92°, bath temperature) for 4 hours. Within 10 minutes crystallization occurred. The product was allowed to cool to room temperature and was stored overnight. After immersing in an ice-bath, the mixture was acidified with HCl, refrigerated 5 hours, filtered, washed with cold (-10°) 1:1 methanol-water and dried. The title compound was obtained as a pale brown solid: 2.776 g, m.p. 300°-310°. (Trituration with hot absolute ethanol gave a pale brown solid in ca 65% recovery, m.p. 320° decomp.)

Workup

  1. temperaturewas heated to 70°
  2. customto give a clear solution
  3. temperaturethe magnetically stirred mixture was heated (90°-92°, bath temperature) for 4 hours
  4. customWithin 10 minutes crystallization
  5. customAfter immersing in an ice-bath
  6. customwas acidified with HCl, refrigerated 5 hours
  7. filtrationfiltered
  8. washwashed with cold (-10°) 1:1 methanol-water
  9. customdried

Sources & evidence

ORD record
ord-551b1dc7055b4193b6f510746d9829e4
Source dataset
uspto-grants-1977_03
Patent number
US04013770

Reaction notes

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