Pyridine → HCID 178450497, compound

HRID 1534469Notes

Reaction equation

HRID 1534469 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][O:21][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:18][CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178450496HCID 178450496, compound

Product 1

HCID 178450497HCID 178450497, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of ethyl 2-butyryl-3-(4-hydroxymethylphenylamino)acrylate (49.5 g, 0.17 mol) and pyridine (50 ml) in chloroform (250 ml) was stirred at 0°-5° (ice-bath). Benzoyl chloride (22 ml, 0.19 mol) in chloroform (250 ml) was added dropwise keeping the reaction temperature below 10° C. Cooling was removed and the mixture was stirred overnight at room temperature. The mixture was washed with 2 M HCl, sodium hydrogen carbonate solution and brine, dried (anhyd. MgSO4), filtered and evaporated to an oil which crystallized on standing. The product was slurried with petroleum ether, filtered off and washed with petroleum ether to give ethyl 2-butyryl-3-(4-benzoyloxymethylphenylamino)acrylate as white crystals (61.8 g, 92%), m.p. 73° C.-5° C.

Workup

  1. customthe reaction temperature below 10° C
  2. temperatureCooling
  3. customwas removed
  4. washThe mixture was washed with 2 M HCl, sodium hydrogen carbonate solution and brine
  5. dry with materialdried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customcrystallized
  9. filtrationfiltered off
  10. washwashed with petroleum ether

Sources & evidence

ORD record
ord-3db9c898af884960a41a6bbaf825c007
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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