Diketene → 4'-chloro-N-methylacetoacetanilide

HRID 224493

Reaktionsgleichung

Reaktionsgleichung von HRID 224493
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1>ClCCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:13](=[O:14])[CH2:12][C:11]([CH3:10])=[O:15])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 12661DiketeneHCID 702724-Chloro-N-methylbenzenamine

Produkt 1

HCID 202975304'-chloro-N-methylacetoacetanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

An appropriately fitted reaction flask was charged with 26.5 g (0.187 mole) of 4-chloro-N-methylaniline [prepared as described by Kadin in The Journal of Organic Chemistry, vol. 38, p. 1348 (1973)] and 90 ml of 1,2-dichloroethane. Dropwise addition of 16.7 g (0.2 mole) of diketene produced an exothermic response. The reaction solution was refluxed for four hours. Additional 1,2-dichloroethane was added and the organic phase was extracted with: (a) dilute hydrochloric acid, (b) water and (c) saturated aqueous sodium chloride. After drying the 1,2-dichloroethane solution over sodium sulfate, the solvent was evaporated under an efficient source of vacuum. The residual oil (38.9 g, 92%) was used in the following reaction without further purification. N.M.R. (CDCl3) ∂1.8 (CH3, enol), 2.2 (CH3, keto), 3.2 (NCH3), 3.7 (CH2), 4.8 (CH), 7.2-7.4 (aromatic).

Aufarbeitung

  1. customAn appropriately fitted reaction flask
  2. customprepared
  3. customproduced an exothermic response
  4. temperatureThe reaction solution was refluxed for four hours
  5. extractionthe organic phase was extracted with: (a) dilute hydrochloric acid, (b) water and (c) saturated aqueous sodium chloride
  6. dry with materialAfter drying the 1,2-dichloroethane solution over sodium sulfate
  7. customthe solvent was evaporated under an efficient source of vacuum
  8. customThe residual oil (38.9 g, 92%) was used in the following reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d2444d05731c40cea21bf9b4de705ffa
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232163

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