Tiopronin → 6-Methyl[1,4]thiazine-2,5-dione

HRID 1577108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1577108
[SH:1][CH:2]([CH3:10])[C:3]([NH:5][CH2:6][C:7](O)=[O:8])=[O:4].C(N(CC)CC)C.ClC(OCC)=O>C(Cl)Cl>[CH3:10][CH:2]1[S:1][C:7](=[O:8])[CH:6]=[N:5][C:3]1=[O:4]

Komponenten

5

Edukt 3

HCID 5483TioproninHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Produkt 1

HCID 212963336-Methyl[1,4]thiazine-2,5-dioneAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N-(2-mercaptopropanoyl) glycine (5 g, 0.031 mole) in methylene chloride (250 ml) was chilled in an ice bath and triethylamine (3.1 g, 0.031 mole) was added. Ethyl chloroformate (3.4 g, 0.031 mole) in methylene chloride (25 ml) was added dropwise over 15 minutes. The resulting solution was then stirred for two and a half hours at room temperature. The methylene chloride was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. Filtration and evaporation of the solvent afforded the crude product as a yellow oil which was chromatographed on silica-gel (CHCl3) to yield colorless crystals of 6-methyl[1,4]thiazine-2,5-dione (1.5 g, 30%) after crystallization from ether-hexane, m.p. 81°-83°.

Aufarbeitung

  1. washThe methylene chloride was washed with water, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and evaporation of the solvent
  4. customafforded the crude product as a yellow oil which
  5. customwas chromatographed on silica-gel (CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-9bdec28671664b01aa8db41627111eb1
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04287203

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