1,1'-Thiocarbonyldiimidazole → 1-(4-Isothiocyanatophenyl)-4-methylpiperazine

HRID 10773

Reaktionsgleichung

Reaktionsgleichung von HRID 10773
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1>CN(C)C=O>[N:26]([C:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]2)=[CH:21][CH:22]=1)=[C:1]=[S:2]

Komponenten

4

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 7372534-(4-Methylpiperazin-1-yl)aniline

Produkt 1

HCID 137183971-(4-Isothiocyanatophenyl)-4-methylpiperazineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A mixture of thiocarbonyldiimidazole (4.46 g, 25.0 mmol) (Aldrich) and N,N-dimethylformamide (20 mL) was cooled to about −15° C. and a solution of 4-(4-methyl-1-piperazinyl)benzenamine (prepared according to the procedure of Chong, W. K. et al. WO9921845; 4.78 g, 25.0 mmol) was added over a period of 30 min. The cooling bath was removed and the mixture was stirred for 1 h. The mixture was cooled to 0° C. and ice-water was added. After 30 min, the mixture was extracted with ether (3×200 mL), dried (Na2SO4), filtered, and evaporated to give 1-(4-isothiocyanatophenyl)-4-methylpiperazine (4.84 g, 83%) as a pale purple solid.

Aufarbeitung

  1. addition4.78 g, 25.0 mmol) was added over a period of 30 min
  2. customThe cooling bath was removed
  3. temperatureThe mixture was cooled to 0° C.
  4. additionice-water was added
  5. waitAfter 30 min
  6. extractionthe mixture was extracted with ether (3×200 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9f2ddd4ffff34606b2cc625dff14a9fc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094896B2

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