N,N-Dimethylaniline → HCID 131711252, Verbindung

HRID 851587

Reaktionsgleichung

Reaktionsgleichung von HRID 851587
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C(N(CC)CC)C.CN(C)C1C=CC=CC=1.[C:37]1([CH2:43][C:44](Cl)=[S:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:44](=[S:45])[CH2:43][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:5]2[S:4]1

Komponenten

6

Edukt 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochlorideHCID 19906501Benzylthiocarbonyl chloride

Produkt 1

HCID 131711252HCID 131711252, VerbindungAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.0 g) was suspended in dried dichloromethane (50 ml) and then dissolved by adding triethylamine (0.72 g) and dimethylaniline (1.9 g) under cooling at -15° C. To a mixture was dropwise added a solution of phenylthioacetyl chloride (2.2 g) in dried dichloromethane (10 ml) under stirring, and the mixture was stirred for 1.5 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 solvent was distilled off, ether was added to the residue, after which the precipitated crystals were collected by filtration and dried to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate (3.4 g), mp 140° to 142° C.

Aufarbeitung

  1. dissolutiondissolved
  2. stirringthe mixture was stirred for 1.5 hours 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. distillationAfter the solvent was distilled off
  7. additionether was added to the residue
  8. filtrationafter which the precipitated crystals were collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dcc77b214b0f4656adb3610d244174a5
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04385176

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