Sodium Hydroxide → 2-(2-Imidazolin-2-yl)methylthio-5-mercapto-1,3,4-thiadiazole hydrochloride

HRID 1073815

Reaktionsgleichung

Reaktionsgleichung von HRID 1073815
[SH:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[OH-].[Na+].Cl.[Cl:11][CH2:12][C:13]1[NH:14][CH2:15][CH2:16][N:17]=1>C(O)C>[ClH:11].[NH:17]1[CH2:16][CH2:15][N:14]=[C:13]1[CH2:12][S:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 27609282-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochlorideHCID 178418558HCID 178418558, Verbindung

Produkt 1

HCID 1784798212-(2-Imidazolin-2-yl)methylthio-5-mercapto-1,3,4-thiadiazole hydrochlorideAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 30 ml of ethanol was suspended 2.25 g of 2,5-dimercapto-1,3,4-thiadiazole, and 30 ml of 1N-sodium hydroxide solution was added to the suspension under ice-cooling and stirring. To the mixture was further added 2.33 g of 2-(chloromethyl)imidazoline hydrochloride, and the mixture was stirred at room temperature for 90 minutes and concentrated under reduced pressure. The concentrate was adjusted to pH 4.8 and washed with ethyl acetate. The aqueous layer was concentrated and subjected to a column chromatography on XAD-II (300 ml), being washed with water and eluted with 10% aqueous ethanol. The eluate was evaporated to dryness under reduced pressure. To the residue were added 50 ml of ethanol and 5 ml of conc hydrochloric acid, and the resultant was stirred. The precipitating crystals were collected by filtration and washed with ethanol to give 2.10 g of 2-(2-imidazolin-2-yl)methylthio-5-mercapto-1,3,4-thiadiazole hydrochloride as colorless crystals (mp 204°-209° C. decomp.).

Aufarbeitung

  1. additionwas added to the suspension under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 90 minutes
  4. concentrationconcentrated under reduced pressure
  5. washwashed with ethyl acetate
  6. concentrationThe aqueous layer was concentrated
  7. washbeing washed with water
  8. washeluted with 10% aqueous ethanol
  9. customThe eluate was evaporated to dryness under reduced pressure
  10. additionTo the residue were added 50 ml of ethanol and 5 ml of conc hydrochloric acid
  11. stirringthe resultant was stirred
  12. filtrationThe precipitating crystals were collected by filtration
  13. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-763a20f83cc04ee5a6e0db3d7549ba66
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971963

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