Pyridine → 1-(p-Fluorocinnamamido)hydantoin

HRID 1579206Notes

Reaction equation

HRID 1579206 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.Cl.[NH2:14][N:15]1[CH2:21][C:19](=[O:20])[NH:18][C:16]1=[O:17].N1C=CC=CC=1>O=S(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH:14][N:15]2[CH2:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])=[O:10])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 124729631-Aminohydantoin hydrochloride

Product 1

HCID 681389071-(p-Fluorocinnamamido)hydantoin

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of p-fluorocinnamic acid (36 g, 0.22 mole) in SOCl2 (75 ml) was heated under reflux with stirring for 1 hour. The excess SOCl2 was removed in vacuo and the residue fluxhed with benzene. To the resulting acid chloride was added 1-aminohydantoin hydrochloride (39 g, 0.26 mole) and 250 ml of pyridine and the resulting reaction mixture was heated on the steam bath for 3 hours. The mixture was poured onto HCl/ice and the product allowed to crystallize.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe excess SOCl2 was removed in vacuo
  4. customthe resulting reaction mixture
  5. temperaturewas heated on the steam bath for 3 hours
  6. additionThe mixture was poured onto HCl/ice
  7. customto crystallize

Sources & evidence

ORD record
ord-c6be25ffe98b4042b5c8d32fc2e25b02
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

Loading…