alpha-Methylcinnamoylchloride → (+/-)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamide

HRID 2105247Notes

Reaction equation

HRID 2105247 reaction equation
[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](Cl)=[O:4].[CH3:13][CH:14]([CH3:28])[CH:15]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[N:16]1[CH:20]=[N:19][CH:18]=[N:17]1>C(Cl)Cl.N1C=CC=CC=1>[CH3:1]/[C:2](=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)/[C:3]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([CH:15]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:14]([CH3:28])[CH3:13])=[CH:22][CH:23]=1)=[O:4]

Participants

5

Reactant 2

HCID 230201alpha-MethylcinnamoylchlorideHCID 10900053(+/-)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine

Product 1

HCID 9885242(+/-)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamideYield 21%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methyl-3-phenyl-2-propenoyl chloride (0.0554 mol) in CH2Cl2 (50 ml) was added dropwise to a solution of (±)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine (0.037 mol) in pyridine (8 ml) and CH2Cl2 (100 ml) and the mixture was stirred at RT for 4 hours. The solvent was evaporated and the residue was taken up in water/EtOAc. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1). The pure fractions were collected and evaporated. The residue was crystallized from (C2H5)2O/methylethylketone, yielding 2.7 g (21%) of (±)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamide (compound 154).

Workup

  1. customThe solvent was evaporated
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1)
  6. customThe pure fractions were collected
  7. customevaporated
  8. customThe residue was crystallized from (C2H5)2O/methylethylketone

Sources & evidence

ORD record
ord-f63a57e8984e4221bcc746961cf2d4b4
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

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