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

HRID 2166311ノート

反応式

HRID 2166311 の反応式
[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

参加物

3

反応物 2

HCID 6561IsobutyraldehydeHCID 76934-Chlorophenyl Isocyanate

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d232fa643f747bcb0b2ab54b7e72ee8
出典データセット
uspto-grants-1990_07
特許番号
US04944795

反応ノート

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