Carbon Disulfide → (2-{[(5-Methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamodithioic acid

HRID 372268

Reaktionsgleichung

Reaktionsgleichung von HRID 372268
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[C:12](=[S:14])=[S:13]>C(O)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12](=[S:13])[SH:14]

Komponenten

4

Edukt 2

HCID 6348Carbon DisulfideHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Produkt 1

HCID 15566013(2-{[(5-Methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamodithioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-((5-methyl-4-imidazolyl)methylthio)ethylamine (10.2 g) in ethanol (75 ml) was added slowly, with stirring, to carbon disulphide (200 ml). The mixture was set aside overnight at room temperature and the solid formed was collected and recrystallised from aqueous isopropyl alcohol to afford N-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]dithiocarbamic acid (9.8 g), m.p. 127°-129°. This was treated with dicyclohexylcarbodiimide in dry pyridine at -10°, and the mixture was filtered. The filtrate was evaporated to dryness and the residue was treated sith ethanolic hydrogen chloride to give 5-methyl-4-(2-isothiocyanatoethylthiomethyl)imidazole hydrochloride.

Aufarbeitung

  1. customthe solid formed
  2. customwas collected
  3. customrecrystallised from aqueous isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-d1d9af87a0e9408d9417ba1c529e7d42
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04090026

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