Thionyl Chloride → HCID 68139171, compound

HRID 1579208Notes

Reaction equation

HRID 1579208 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=O.S(Cl)(Cl)=O.Cl.[NH2:18][N:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[O:21]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([NH:18][N:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[O:21])=[O:9]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 886063-(3-Fluorophenyl)-2-propenoic acidHCID 124729631-Aminohydantoin hydrochloride

Product 1

HCID 68139171HCID 68139171, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 99.5 g (0.6 mole) of m-fluorocinnamic acid was added dropwise thionyl chloride (600 ml) followed by heating at reflux for 2 hours. The excess thionyl chloride was removed in vacuo and the residue remaining flushed with dry benzene. The reaction residue was chilled on an ice bath followed by the rapid addition of 1-aminohydantoin hydrochloride (91 g, 0.6 mole). To the cold reaction mixture was added dropwise pyridine (600 ml). After the addition was complete the cold reaction mixture was heated on a steam bath for 3 hours then poured into 6 l. of HCl/ice. Upon standing at room temperature overnight the acidic reaction mixture was filtered and washed with water to give 116 g (73.5%) which after recrystallization from CH3NO2 melted at 294°-296°.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 2 hours
  3. customThe excess thionyl chloride was removed in vacuo
  4. customthe residue remaining flushed with dry benzene
  5. temperatureThe reaction residue was chilled on an ice bath
  6. customTo the cold reaction mixture
  7. additionAfter the addition
  8. customthe cold reaction mixture
  9. temperaturewas heated on a steam bath for 3 hours
  10. additionthen poured into 6 l
  11. filtrationthe acidic reaction mixture was filtered
  12. washwashed with water
  13. customto give 116 g (73.5%) which
  14. customafter recrystallization from CH3NO2 melted at 294°-296°

Sources & evidence

ORD record
ord-073c5e4d903946c6a57159610091f647
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

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