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N,N-Dimethylaniline → HCID 12833985, Verbindung

HRID 851594
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 851594
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][CH:8]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[N:11]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3C=C[CH:30]=[CH:29][CH:28]=3)[C@H:10]2[S:9]1.CN(C)C1C=CC=CC=1.[S:44]1C=CC=C1CC(Cl)=O>ClCCl.CO.N1C=CC=CC=1>[CH3:7][CH:8]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:20])[Cl:21])=[O:15])[N:11]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[S:44][CH:30]=[CH:29][CH:28]=3)[C@H:10]2[S:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 1623622-Thiopheneacetyl chlorideHCID 705273932,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

Produkt 1

HCID 12833985HCID 12833985, VerbindungAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel
HCID 1049PyridineLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Pyridine (0.296 g) and phosphorous pentachloride (0.616 g) were added in turn under stirring and cooling at -15° C. to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (1.12 g), mp 175° to 178° C., in dried dichloromethane (20 ml), and the mixture was stirred for 20 minutes at the same temperature and further for 2 hours at room temperature. To the mixture was added absolute methanol (5 ml) under cooling at -15° C., and then the mixture was stirred for 1 hour at the same temperature. To the mixture were dropwise added in turn dimethylaniline (2.2 g) and a solution of 2-thienylacetyl chloride (0.42 g) in dried dichloromethane (5 ml) at the same temperature, and then the mixture was stirred for 2.5 hours at the same temperature. After the reaction, the reaction mixture was in turn washed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water, and then dried. After the solution was concentrated, the obtained oily substance was crystallized by adding ether to give 2,2,2-trichloroethyl 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylate (750 mg), mp 161° to 162° C. (dec.).

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes at the same temperature and further for 2 hours at room temperature
  2. stirringthe mixture was stirred for 1 hour at the same temperature
  3. customAfter the reaction
  4. washwashed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water
  5. customdried
  6. concentrationAfter the solution was concentrated
  7. customthe obtained oily substance was crystallized
  8. additionby adding ether

Quellen und Nachweise

ORD-Eintrag
ord-b63d692f3d98402e90a29c07ee10375b
Quelldatensatz
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04385176

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