Thiazole → 2,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazin

HRID 1381901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381901
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[S:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[CH3:12][O:13][C:14]1([O:22][CH3:23])[C:19](=O)[NH:18][C:17]([CH3:21])=[CH:16][S:15]1>ClCCl>[CH3:23][O:22][C:14]1([O:13][CH3:12])[CH:19]=[N:18][C:17]([CH3:21])=[C:16]([CH:8]2[N:9]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:10]=[CH:11][S:7]2)[S:15]1

Komponenten

5

Edukt 3

HCID 9256ThiazoleHCID 10928Ethyl chloroformateHCID 143697992,2-dimethoxy-5-methyl-4H-1,4-thiazin-3-one

Produkt 1

HCID 867427442,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazinAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl chloroformate (1.0 g) was added dropwise to a stirred solution of thiazole (0.79 g) in dichloromethane (10 ml) under ice-cooling and the mixture was stirred at room temperature for 0.5 hour. Then, 2,2-dimethoxy-5-methyl-2H-1,4-thiazin-3(4H)-one (1.47 g) was added, and the mixture was stirred at room temperature for 3 hours. The solution was washed with saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel (Merck Lobar column size B: Art.10401, solvent: ethyl acetate-n-hexane=2:3) to give 2,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazin-(4H-one (510 mg, yield 19%) as colorless prisms.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. washThe solution was washed with saturated sodium bicarbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel (Merck Lobar column size B: Art.10401, solvent: ethyl acetate-n-hexane=2:3)

Quellen und Nachweise

ORD-Eintrag
ord-340368a6d3b84bbea1772620aeb1dd0c
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04804668

Notizen zur Reaktion

Wird geladen…