1,1'-Thiocarbonyldiimidazole → 1-(Acetyl)-4-(4-isothiocyanatophenyl)piperazine

HRID 10780

Reaktionsgleichung

Reaktionsgleichung von HRID 10780
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:17](N1C=CN=C1)(N1C=CN=C1)=[S:18]>CN(C)C=O>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[S:18])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

Produkt 1

HCID 219588991-(Acetyl)-4-(4-isothiocyanatophenyl)piperazineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A solution of 1-acetyl-4-(4-aminophenyl)piperazine (1.0 g, 4.6 mmol) (from Step B above) in N,N-dimethylformamide (10 mL) was added dropwise to a cooled (−15° C.) solution of thiocarbonyldiimidazole (855 mg, 4.8 mmol) in N,N-dimethylformamide (10 mL). After the addition was complete, the mixture was stirred at −15° C. for 30 min, then the cooling bath was removed and the solution was stirred for 1 h. Ice-water was added and the mixture was extracted with ether (4×50 mL). The combined ether layers were washed with brine, dried (MgSO4), filtered, and evaporated to give 1-(acetyl)-4-(4 isothiocyanatophenyl)piperazine (1.0 g, 84%).

Aufarbeitung

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 h
  4. additionIce-water was added
  5. extractionthe mixture was extracted with ether (4×50 mL)
  6. washThe combined ether layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-791ac1550fd64af8a5667939b1f90372
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094896B2

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