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Hydrochloric Acid → N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

HRID 256769
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 256769
[CH3:1][NH:2][CH:3]=[O:4].C(N(CC)CC)C.ClC(OC(Cl)=O)(Cl)Cl.[O:20]([C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(Cl)(Cl)=O.Cl>C1(C)C=CC=CC=1.O.CC(C)=O>[CH3:1][NH:2][C:3](=[O:4])[C:29]([C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10426DiphosgeneHCID 24386Thionyl ChlorideHCID 31254N-MethylformamideHCID 752372-Phenoxybenzoic acid

Produkt 1

HCID 11780091
N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide
Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

N-Methylformamide (2.36 g, 40.0 mmol) and triethyl amine (8.08 g, 80.0 mmol) were dissolved in toluene (40 ml). Trichloromethylchloroformate (3.96 g, 20.0 mmol) was added dropwise slowly under ice-cooling while maintaining the inner temperature at 10° C. or lower. The mixture was stirred at the same temperature for 1 hour. A large amount of insoluble materials were precipitated. To the mixture was added 2-phenoxybenzoyl chloride which was prepared from 2-phenoxybenzoic acid (4.28 g, 20.0 mmol) and thionyl chloride (2.86 g, 24.0 mmol). The resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours. 5N-Hydrochloric acid (12 ml) and acetone (20 ml) were added, and the mixture was stirred for 12 hours. Water was added to the mixture, which was then extracted with toluene and purified by column chromatography on silica gel to obtain the title compound (3.11 g, Yield: 61.0%).

Aufarbeitung

  1. temperaturecooling
  2. customA large amount of insoluble materials were precipitated
  3. additionTo the mixture was added 2-phenoxybenzoyl chloride which
  4. stirringThe resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours
  5. stirringthe mixture was stirred for 12 hours
  6. extractionwas then extracted with toluene
  7. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fce1158198784bd78811a8322f558a03
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05258551

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