Lawesson's reagent → 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepine-5(4H)-thione

HRID 4813

Reaktionsgleichung

Reaktionsgleichung von HRID 4813
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=O)[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[S:5]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:26])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[S:5]1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 137264572-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one

Produkt 1

HCID 137264582-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepine-5(4H)-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4.3 g (0.017 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]thiazepin-5(4H)-one, 100 ml of toluene and 4.8 g (0.012 mole) of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was refluxed for 3 hr and then extracted twice with dilute sodium hydroxide. The organic layer was concentrated and the residue chromatographed on the high pressure liquid chromatograph using a silica column and 50% ethyl acetate-50% hexane. The yield of title compound was 2 g, m.p. 160°-162° C.

Aufarbeitung

  1. temperaturewas refluxed for 3 hr
  2. extractionextracted twice with dilute sodium hydroxide
  3. concentrationThe organic layer was concentrated
  4. customthe residue chromatographed on the high pressure liquid chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-2835159553ab4fcdb331894bd71cc090
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727152

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