Hydrochloric Acid → 2-Acetyl-3-methyl-N-phenylbutanamide

HRID 364927

反応式

HRID 364927 の反応式
[H-].[Na+].[C:3]([CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])(=[O:5])[CH3:4].[H][H].Br[CH:19]([CH3:21])[CH3:20].Cl>CN(C)C=O.O>[C:3]([CH:6]([CH:19]([CH3:21])[CH3:20])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])(=[O:5])[CH3:4]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 7592AcetoacetanilideHCID 24758Sodium hydrideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 136209742-Acetyl-3-methyl-N-phenylbutanamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (0.48 g. of a 50% w/w dispersion in mineral oil) was added to a solution of 2-acetylacetanilide (1.8 g.) in dry dimethylformamide (15 ml.) under an atmosphere of argon. The mixture was stirred at 35° until the evolution of hydrogen had ceased. 2-Bromopropane (1.12 ml.) was added, and the mixture was heated at 55°-60° for 110 hr. The mixture was cooled and then poured into water (100 ml.). The resulting solution was adjusted to pH 2 with 3N-hydrochloric acid and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was dried (Na2SO4) and the ethyl acetate was evaporated in vacuo. The residual oil was chromatographed on silica gel (Kieselgel 60, 180 g.) using 20% v/v ethyl acetate in petroleum ether (b.p. 60°-80°) as eluant. The relevant fraction was evaporated in vacuo, and the residue was crystallised from cyclohexane to give 2-acetyl-2-isopropylacetanilide, m.p. 135°-7° .

後処理

  1. temperaturethe mixture was heated at 55°-60° for 110 hr
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×100 ml.)
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. customthe ethyl acetate was evaporated in vacuo
  7. customThe residual oil was chromatographed on silica gel (Kieselgel 60, 180 g.)
  8. customThe relevant fraction was evaporated in vacuo
  9. customthe residue was crystallised from cyclohexane

出典と根拠

ORDレコード
ord-0ae5e63111934a17ad364d2600bc8388
出典データセット
uspto-grants-1986_08
特許番号
US04607039

関連ノート

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