Pyridine → HCID 19875859, compound

HRID 1086206Notes

Reaction equation

HRID 1086206 reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[N:4]1[CH:8]=[N:7][CH:6]=[N:5]1.N1C=CC=CC=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](Cl)=[O:35])=[CH:29][CH:28]=1>ClCCl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([CH:3]([N:4]3[CH:8]=[N:7][CH:6]=[N:5]3)[CH:2]([CH3:19])[CH3:1])=[CH:10][C:11]=2[N+:16]([O-:18])=[O:17])=[O:35])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 906924-Chlorophenylacetyl chlorideHCID 19875831HCID 19875831, compound

Product 1

HCID 19875859HCID 19875859, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (5° C.) solution of 10 parts of 4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-2-nitrobenzenamine and 6.7 parts of pyridine in 195 parts of dichloromethane was added a solution of 14.4 parts of 4-chlorobenzeneacetyl chloride in 39 parts of dichloromethane under nitrogen atmosphere. After stirring overnight at room temperature, the reaction mixture was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (99:1 by volume) as eluent. The eluent of the desired fraction was evaporated, yielding 11 parts (69.9%) of 4-chloro-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-2-nitrophenyl]benzeneacetamide (interm. 112).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washthe reaction mixture was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (99:1 by volume) as eluent
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-6eba9c8427ba4e2e976a30de79086ba2
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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