Pyridine → HCID 178450481, compound

HRID 1647472Notes

Reaction equation

HRID 1647472 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([OH:22])[CH3:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([O:22][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:21])[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 178450483HCID 178450483, compound

Product 1

HCID 178450481HCID 178450481, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2-butyryl-3-(2-(1-hydroxyethyl)-phenylamino)acrylate (63 g, 0.2 mol) and pyridine (50 ml in dichloromethane (400 ml) were stirred at 0° C. and treated with benzoyl chloride (50 ml) in dichloromethane (100 ml) added at such a rate to keep the reaction temperature below 10° C. The cooling bath was removed and the mixture was stirred at ambient temperature for 2 hours. The solution was washed with 2M hydrochloric acid (×2), saturated sodium hydrogen carbonate solution, water and brine, dried (anhyd. MgSO4), filtered and evaporated-to an orange oil (70 g, 83%).

Workup

  1. additionadded at such a rate
  2. customthe reaction temperature below 10° C
  3. customThe cooling bath was removed
  4. washThe solution was washed with 2M hydrochloric acid (×2), saturated sodium hydrogen carbonate solution, water and brine
  5. dry with materialdried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated-to an orange oil (70 g, 83%)

Sources & evidence

ORD record
ord-d1ad8ad1fac44a818d9f857d09afaaaf
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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