2-Chlorobenzaldehyde → HCID 21276949, compound

HRID 2292138Notes

Reaction equation

HRID 2292138 reaction equation
[C:1]([NH:5][C:6](=[O:11])/[CH:7]=[C:8](\[NH2:10])/[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O.[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[CH2:31][CH2:32][CH2:33][O:34][CH2:35][C:36](=O)[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C(O)C>[C:1]([NH:5][C:6]([C:7]1[CH:15]([C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[Cl:12])[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:36]([CH2:35][O:34][CH2:33][CH2:32][CH2:31][C:23]2[N:22]([CH3:21])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=2)[NH:10][C:8]=1[CH3:9])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 19864533HCID 19864533, compoundHCID 21276958HCID 21276958, compound

Product 1

HCID 21276949HCID 21276949, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-t-Butyl-3-aminocrotonamide (0.63 g), 2-chlorobenzaldehyde (0.56 g) and ethyl 4-[3-(1-methylbenzimidazol-2-yl)propoxy]-3-ketobutanoate (1.27 g) were dissolved in ethanol (16 ml) and stirred under reflux for 15 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The residue was chromatographed on silica eluting with 3% methanol in ethyl acetate. The fractions containing the product were combined and evaporated. Recrystallisation of the resulting foam from ethanol yielded the title compound as a white solid (0.33 g, 14%), m.p. 202° C. Found: C, 66.17; H, 6.92; N, 9.48. C32H39ClN4O4 requires C, 66.36; H, 6.79; N, 9.68%.

Workup

  1. temperatureunder reflux for 15 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica eluting with 3% methanol in ethyl acetate
  5. additionThe fractions containing the product
  6. customevaporated
  7. customRecrystallisation of the resulting foam from ethanol

Sources & evidence

ORD record
ord-c27ae321195640029b193d16ba75816b
Source dataset
uspto-grants-1989_01
Patent number
US04801598

Reaction notes

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