Water → HCID 298384, compound

HRID 1703627Notes

Reaction equation

HRID 1703627 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:8](=O)[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.O>C(O)(=O)C>[CH:8](=[C:7]1[NH:1][C:2](=[O:3])[NH:4][C:5]1=[O:6])[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7362FurfuralHCID 10006Hydantoin

Product 1

HCID 298384HCID 298384, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of hydantoin (10 g), fused sodium acetate (20 g), and freshly distilled furfural (12 g) in acetic acid (40 ml) was heated under reflux for 11/4 hours. The dark solution was poured into cold water (400 ml) to precipitate the dark green/yellow product, which was washed with water until neutral and then with cold ethanol to give 14 g (80% theoretical yield) of 5-furfurylidenehydantoin m.p. 232°-5° (decomp.) (H. L. Wheeler and C. Hoffman, Amer. Chem. J., 1911, 45, 368, quote m.p. 232°.) The material was used without further purification.

Workup

  1. temperatureunder reflux for 11/4 hours
  2. customto precipitate the dark green/yellow product, which
  3. washwas washed with water until neutral and then with cold ethanol

Sources & evidence

ORD record
ord-965a3751b98a4fae99a66df11f1ba330
Source dataset
uspto-grants-1978_11
Patent number
US04124760

Reaction notes

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