Ethanethiol → HCID 53629164, Verbindung

HRID 1896389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896389
[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH3:11])[C:7]=1[C:8](O)=[O:9])#[N:2].[CH2:12]([SH:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([C:3]1[N:4]=[CH:5][N:6]([CH3:11])[C:7]=1[C:8](=[O:9])[S:14][CH2:12][CH3:13])#[N:2]

Komponenten

6

Edukt 3

HCID 6343Ethanethiol2×HCID 10868DicyclohexylcarbodiimideHCID 450820154-Cyano-1-methyl-1H-imidazole-5-carboxylic acid

Produkt 1

HCID 53629164HCID 53629164, VerbindungAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 1 l, three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, 4-cyano-1-methyl-1H-imidazole-5-carboxylic acid x84 (24.5 g, 0.162 mol) and CH2Cl2 (500 ml) are stirred at room temperature. To this suspension, ethanethiol (13.2 ml, 0.178 mol) and DMAP (1.98 g, 0.016 mol) are added, followed by DCC (36.77 g, 0.178 mol) in two portions. The temperature rises to 35° C. and the mixture is stirred at room temperature for 16 h. Ethanethiol (0.0324 mol) is further added and stirring is continued overnight. The mixture is filtered and the solvent is evaporated. The residue is purified by chromatography on silicagel (Hexane/AcOEt: 6/4 (v/v)) to give 29.5 g of S-ethyl 4-cyano-1-methyl-1H-imidazole-5-carbothioate x85.

Aufarbeitung

  1. customrises to 35° C.
  2. stirringthe mixture is stirred at room temperature for 16 h
  3. stirringstirring
  4. filtrationThe mixture is filtered
  5. customthe solvent is evaporated
  6. customThe residue is purified by chromatography on silicagel (Hexane/AcOEt: 6/4 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-03ae3ef13fbd42528be0d4dd6bee2109
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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