Isobutyraldehyde → N-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanamide

HRID 2166311Notes

Reaction equation

HRID 2166311 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH:11](=[O:15])[CH:12]([CH3:14])[CH3:13]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[C:12]([CH3:14])([CH3:13])[CH:11]=[O:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6561IsobutyraldehydeHCID 76934-Chlorophenyl Isocyanate

Product 1

HCID 15085728N-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanamideYield 67.8%

Procedure

p-Chlorophenyl isocyanate (21.08 g) and the morpholinoenamide of isobutyraldehyde (38.7 g) were stirred together in a 100 mL round bottom flask. After an initial exotherm, the solution was allowed to stir at ambient temperature overnight. The excess enamine was then removed in vacuo at 60° C., and the residue was taken up in ether and hexane added. The material was filtered to remove an unwanted urea side product, then the filtrate was washed with dilute HCl, and additional ether was added to redissolve some precipitated product. The organic layer was then dried and concentrated in vacuo to give a solid. Recrystallization furnished 21 g of N-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanamide, m.p. 99°-100° C.

Workup

  1. customThe excess enamine was then removed in vacuo at 60° C.
  2. additionhexane added
  3. filtrationThe material was filtered
  4. customto remove an unwanted urea side product
  5. washthe filtrate was washed with dilute HCl, and additional ether
  6. additionwas added
  7. dissolutionto redissolve some precipitated product
  8. customThe organic layer was then dried
  9. concentrationconcentrated in vacuo
  10. customto give a solid
  11. customRecrystallization

Sources & evidence

ORD record
ord-3d232fa643f747bcb0b2ab54b7e72ee8
Source dataset
uspto-grants-1990_07
Patent number
US04944795

Reaction notes

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