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1-Bromo-2-butanone → N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide

HRID 486295
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 486295
[CH:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:20]([C:22]([CH2:24]Br)=[O:23])[CH3:21].[Cl:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](Cl)=[O:35])[CH:30]=[CH:31][CH:32]=1>C1(C)C=CC=CC=1.O.N1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([N:7]([CH2:24][C:22](=[O:23])[CH2:20][CH3:21])[C:34](=[O:35])[CH2:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 131561-Bromo-2-butanoneHCID 81531DiisopropylethylamineHCID 4586793-IsopropylanilineHCID 106552492-(3-chlorophenyl)acetyl Chloride

Produkt 1

HCID 11783283N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 1049PyridineLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

200 g (1.48 mol) of m-isopropylaniline were dissolved in 600 ml of toluene, and 284 ml of diisopropylethylamine were then added thereto. The solution was heated to 45° C. under a nitrogen stream, and 245.8 g (1.63 mols) of bromomethyl ethyl ketone were added dropwise over 3 hours. After the temperature of the solution was returned to room temperature, 132 ml of pyridine were added thereto, and 308 g (1.63 mols) of m-chlorophenylacetyl chloride were then added dropwise thereto. The reaction mixture was poured into water, and the resultant organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 492.8 g of a crude product in an oily state (yield: 93.0%).

Aufarbeitung

  1. additionwere added dropwise over 3 hours
  2. customwas returned to room temperature
  3. customthe resultant organic layer was separated
  4. washwashed with an aqueous saturated sodium bicarbonate solution and water in this order
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e394e961de704dcb969ddcf2e43f2d4a
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05290949

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