2-Chlorobenzaldehyde → HCID 20026681, compound

HRID 1723035Notes

Reaction equation

HRID 1723035 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:22])/[CH:18]=[C:19](\[NH2:21])/[CH3:20].[CH3:23][C:24]1[N:28]([CH2:29][CH2:30][O:31][CH2:32][C:33](=O)[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:27]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:26][N:25]=1>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:18]([C:17](=[O:22])[NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)=[C:19]([CH3:20])[NH:21][C:33]([CH2:32][O:31][CH2:30][CH2:29][N:28]2[C:27]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[N:26][N:25]=[C:24]2[CH3:23])=[C:34]1[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 6033189HCID 6033189, compoundHCID 20026676HCID 20026676, compound

Product 1

HCID 20026681HCID 20026681, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chlorobenzaldehyde (0.3 g, 2.12 mmole), N-(pyrid-2-yl)-3-aminocrotonamide (0.38 g, 2.12 mmole) (obtained from N-(pyrid-2-yl)-3-oxobutanamide by reaction with ethanolic ammonia at room temperature for 16 hours) and ethyl 4-[2-(3-methyl-5-phenyl-4H-1,2,4-triazol-4-yl)ethoxy]-3-oxobutanoate (0.7 g, 2.12 mmole) were dissolved in absolute ethanol (25 ml) and the mixture heated under reflux for 5 hours. The solution was cooled and concentrated to dryness under reduced pressure. The residue was chromatographed on silica, eluting with ethyl acetate containing 15% ethanol. Appropriate fractions were combined, concentrated under vacuum and the residue triturated with ethyl acetate to yield the title product as a white amorphous solid (0.23 g, 20%), m.p. 167°-169° C. Found: C,64.92; H,5.61; N,13.39. C33H33ClN6O4 requires C,64.65; H,5.43; N,13.71%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution was cooled
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was chromatographed on silica
  6. washeluting with ethyl acetate containing 15% ethanol
  7. concentrationconcentrated under vacuum
  8. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-5212d33591d84356a1d6569a861567a0
Source dataset
uspto-grants-1989_08
Patent number
US04859686

Reaction notes

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