HCID 2778117, compound → HCID 68139075, compound

HRID 1579205Notes

Reaction equation

HRID 1579205 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][C:3]=1[C:13]([F:16])([F:15])[F:14].Cl.[NH2:18][N:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[O:21]>O=S(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][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:4][C:3]=1[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 2

HCID 2778117HCID 2778117, compoundHCID 124729631-Aminohydantoin hydrochloride

Product 1

HCID 68139075HCID 68139075, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A stirred mixture of 4-chloro-3-trifluoromethylcinnamic acid (50 g, 0.2 mole) in 200 ml of SOCl2 was heated at reflux for 2 hours. The excess SOCl2 was removed in vacuo and the residue flushed with dry benzene. The residue was treated with a mixture of 1-aminohydantoin hydrochloride (30 g, 0.2 mole) in 400 ml of pyridine. The reaction mixture was heated at reflux for 3 hours; then poured into ice/HCl. The crude residue (74 g, 100%) was recrystallized from CH3NO2 (Darco) to give an analytical sample melting at 270°-273°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe excess SOCl2 was removed in vacuo
  4. customthe residue flushed with dry benzene
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 3 hours
  7. customThe crude residue (74 g, 100%) was recrystallized from CH3NO2 (Darco)
  8. customto give an analytical sample melting at 270°-273°

Sources & evidence

ORD record
ord-0fddd1050c3c408f8838e062af7fa173
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

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