Pyridine → HCID 18510669, compound

HRID 1370257Notes

Reaction equation

HRID 1370257 reaction equation
[N:1]1[CH:6]=CC=C(C=O)C=1.ClN1C(=[O:15])CCC1=O.[C:17]([C:25]1[CH:36]=[CH:35][C:28]([C:29]([NH:31][CH2:32][CH:33]=[CH2:34])=[O:30])=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)(Cl)Cl>[C:17]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:31][CH2:32][CH:33]2[O:15][N:1]=[C:6]([C:46]3[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=3)[CH2:34]2)=[O:30])=[CH:35][CH:36]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 103713-PyridinecarboxaldehydeHCID 31398ChlorosuccinimideHCID 2529944HCID 2529944, compound

Product 1

HCID 18510669HCID 18510669, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Pyridinecarboxaldehyde, oxime (0.013 mol) was added to a suspension of 1-chloro-2,5 pyrrolidinedione (0.0148 mol) in CHCl3 (80 ml) and pyridine (0.16 ml), stirred at RT. The mixture was stirred for 3 hours at 40° C., then cooled to 0° C. and 4-benzoyl-N-(2-propenyl)benzamide (0.011 mol) was added. Then, triethylamine (2.25 ml) was added dropwise and the resulting reaction mixture was stirred overnight at RT. The reaction mixture was washed with water, dried (Na2SO4), filtered and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 2.0 g (37%) of (±)-4-benzoyl-N-[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]methyl]benzamide. (compound 343).

Workup

  1. stirringThe mixture was stirred for 3 hours at 40° C.
  2. temperaturecooled to 0° C.
  3. customthe resulting reaction mixture
  4. stirringwas stirred overnight at RT
  5. washThe reaction mixture was washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-eb5b7fb03f5942f5b8778fb65cc14223
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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