Pyridine → HCID 68139206, compound

HRID 1579207Notes

Reaction equation

HRID 1579207 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH3:14])[CH:5]=[CH:6][C:7]([OH:9])=O.Cl.[NH2:16][N:17]1[CH2:23][C:21](=[O:22])[NH:20][C:18]1=[O:19].N1C=CC=CC=1>O=S(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH3:14])[CH:5]=[CH:6][C:7]([NH:16][N:17]1[CH2:23][C:21](=[O:22])[NH:20][C:18]1=[O:19])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 124729631-Aminohydantoin hydrochlorideHCID 53927079HCID 53927079, compound

Product 1

HCID 68139206HCID 68139206, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

3-Chloro-4-ethylcinnamic acid (50 g, 0.24 mole) in SOCl2 (100 ml) was heated under reflux for about 1 hour. The excess SOCl2 was removed in vacuo and the residue flushed with benzene. The acid chloride was treated with 1-aminohydantoin hydrochloride (40 g, 0.26 mole) and pyridine (300 ml) and the reaction mixture heated on a steam bath for 4 hours. The reaction mixture was poured onto HCl/ice to precipitate the product. (40 g, 55%). Several recrystallizations from CH3NO2 provided analytical material which melted at 231°-234°.

Workup

  1. temperatureunder reflux for about 1 hour
  2. customThe excess SOCl2 was removed in vacuo
  3. customthe residue flushed with benzene
  4. temperaturethe reaction mixture heated on a steam bath for 4 hours
  5. additionThe reaction mixture was poured onto HCl/ice
  6. customto precipitate the product
  7. customSeveral recrystallizations from CH3NO2 provided analytical material which melted at 231°-234°

Sources & evidence

ORD record
ord-41cafb5ca56f4d7cac22d0d4d6b03137
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

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