1,1'-Thiocarbonyldiimidazole → 1-(4-Isothiocyanatophenyl)-4-(sec-butyl)piperazine

HRID 10790

Reaktionsgleichung

Reaktionsgleichung von HRID 10790
[CH:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)([CH2:3][CH3:4])[CH3:2].[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19]>CN(C)C=O>[N:17]([C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)=[C:18]=[S:19]

Komponenten

4

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 219589174-[4-(Sec-butyl)-1-piperazinyl]benzenamine

Produkt 1

HCID 98568281-(4-Isothiocyanatophenyl)-4-(sec-butyl)piperazineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A solution of 4-[4-(sec-butyl)-1-piperazinyl]benzenamine (3.5 g, 15 mmol) (from Step B above) in N,N-dimethylformamide (40 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (2.68 g, 15.03 mmol) (Aldrich) in N,N-dimethylformamide (15 mL). After the addition was complete, the mixture was stirred at −15° C. for 20 min, then the cooling bath was removed and the solution was stirred for 1 h. Ice-water (800 ml) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with water and dried under vacuum to give 1-(4-isothiocyanatophenyl)-4-(sec-butyl)piperazine (3.6 g, 87%) as a purple solid.

Aufarbeitung

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 h
  4. additionIce-water (800 ml) was added
  5. stirringthe mixture was stirred for 30 min
  6. filtrationThe solid was filtered off
  7. washwashed with water
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0384dff13c2340f491f72741cfa3d6a8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094896B2

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