Pyridine → HCID 54062454, compound

HRID 2081607Notes

Reaction equation

HRID 2081607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27]1([CH:33]=[CH:34][C:35](Cl)=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:35](=[O:36])[CH:34]=[CH:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 660233-Phenylprop-2-enoyl chlorideHCID 19967102HCID 19967102, compound

Product 1

HCID 54062454HCID 54062454, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred and cooled (0° C.) mixture of 14.6 parts of 4-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]benzenamine, 60.9 parts of benzene and 6.86 parts of pyridine was added a solution of 10.6 parts of 3-phenyl-2-propenoyl chloride in 17.4 parts of benzene under a nitrogen atmosphere. After stirring overnight at room temperature, the reaction mixture was basified and extracted with ethyl acetate. The extract was washed with water, dried, filtered and evaporated. The residue was crystallized from dichloromethane. The product was filtered off and dried, yielding 17.7 parts (83.8%) of N-[4-[(4-chlorophenyl) (1H-imidazol-1-yl)methyl]phenyl]3-phenyl-2-propenamide; mp. 244° C. (interm. 50). In a similar manner there were also prepared the intermediates listed in Table 3:

Workup

  1. temperaturecooled
  2. stirringAfter stirring overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from dichloromethane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-0555cecef04c43f2a7d83d754345894e
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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