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

HRID 2166311노트

반응식

HRID 2166311 반응식
[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

참가 물질

3

반응물 2

HCID 6561IsobutyraldehydeHCID 76934-Chlorophenyl Isocyanate

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d232fa643f747bcb0b2ab54b7e72ee8
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04944795

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