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

HRID 353729

Reaktionsgleichung

Reaktionsgleichung von HRID 353729
[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 thiocarbonyidiimidazole (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-f81269552cdb4ae68dca973db00b2c96
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756374B2

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