Hydrochloric Acid → HCID 68137776, compound

HRID 1579204Notes

Reaction equation

HRID 1579204 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.Cl.[NH2:18][N:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[O:21].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH:18][N:19]2[CH2:25][C:23](=[O:24])[NH:22][C:20]2=[O:21])=[O:10])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-HCID 24386Thionyl Chloride2×HCID 124729631-Aminohydantoin hydrochloride

Product 1

HCID 68137776HCID 68137776, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-chlorocinnamic acid (46 g, 0.25 mole) was added dropwise SOCl2 (140 ml). The mixture was heated under reflux for 45 minutes after the addition was complete. After stirring at room temperature for 1 hour the SOCl2 was removed in vacuo. Dry benzene was added and then removed in vacuo. The acid chloride residue was treated with 1-aminohydantoin hydrochloride (42 g, 0.275 mole) in 350 ml of pyridine, then heated under reflux for 2 hrs. After cooling slightly, the reaction mixture was poured into a mixture of 200 ml of con HCl and 1500 ml of ice. After standing overnight the product was removed by filtration and washed with H2O. Recrystallization from NaOH/dimethylformamide (H2O) provided analytical material which melted at 230°-235° (25 g, 36%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. additionafter the addition
  4. customwas removed in vacuo
  5. additionDry benzene was added
  6. customremoved in vacuo
  7. temperatureheated
  8. temperatureunder reflux for 2 hrs
  9. temperatureAfter cooling slightly
  10. customthe product was removed by filtration
  11. washwashed with H2O
  12. customRecrystallization from NaOH/dimethylformamide (H2O)
  13. customprovided analytical material which melted at 230°-235° (25 g, 36%)

Sources & evidence

ORD record
ord-7ad3c3cdcb794f3798c6c164e1e59e34
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

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