Benzoyl chloride → HCID 178450495, compound

HRID 1647453Notes

Reaction equation

HRID 1647453 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=1)[CH3:2].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178450494HCID 178450494, compound

Product 1

HCID 178450495HCID 178450495, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (ice-bath) solution of ethyl-2-butyryl-3-(3-hydroxymethylphenylamino)acrylate (29.13 g, 0.1 mol) in pyridine was added dropwise benzoyl chloride (21.09 g, 0.15 mol). The ice bath was removed and the mixture stood for 16 hours, then evaporated, treated with chloroform (200 ml) and washed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml), and 2N hydrochloric acid (2×150 ml). After drying (Na2SO4) and stirring with charcoal, the solution was filtered and evaporated to an oil, which crystallised slowly under petroleum ether (b.p. 40-60) to give the title compound (34.5 g) m.p. 59°-63°.

Workup

  1. customThe ice bath was removed
  2. customevaporated
  3. additiontreated with chloroform (200 ml)
  4. washwashed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml), and 2N hydrochloric acid (2×150 ml)
  5. dry with materialAfter drying (Na2SO4)
  6. stirringstirring with charcoal
  7. filtrationthe solution was filtered
  8. customevaporated to an oil, which
  9. customcrystallised slowly under petroleum ether (b.p. 40-60)

Sources & evidence

ORD record
ord-8909aa5b07454aabb63621218af7d1ed
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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