Benzaldehyde → 5-Benzylidenehydantoin

HRID 1905810Notes

Reaction equation

HRID 1905810 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(CN)O.Cl>O>[CH:8](=[C:7]1[NH:1][C:2](=[O:3])[NH:4][C:5]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 700EthanolamineHCID 10006Hydantoin

Product 1

HCID 978575-BenzylidenehydantoinYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

50 g (0.5 mole) of hydantoin, 55 g (52 ml, 0.52 mole) of benzaldehyde and 46 g (45 ml, 0.7 mole of ethanol amine are admixed in 500 ml of water at 70° C. The temperature is raised to 90° C. and the reaction mixture is stirred for 4 hours. The solution is cooled and acidified with concentrated hydrochloric acid (pH 3-4). The mixture is allowed to stand at 10° C. for an hour, the product is filtered off, washed with cold water and dried. Thus 84.5 g of the desired compound are obtained, yield 89%. Mp.: 220°-222° C.

Workup

  1. temperatureThe solution is cooled
  2. waitto stand at 10° C. for an hour
  3. filtrationthe product is filtered off
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-00a5c5b298034c73b98ecc89fcebaaf7
Source dataset
uspto-grants-1987_03
Patent number
US04647694

Reaction notes

Loading…