1,1'-Thiocarbonyldiimidazole → 4-(4-Isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester

HRID 10783

Reaktionsgleichung

Reaktionsgleichung von HRID 10783
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22]>CN(C)C=O>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)=[C:21]=[S:22]

Komponenten

4

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

Produkt 1

HCID 185218234-(4-Isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl esterAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 4-(4-aminophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (15 g, 54.1 mmol) (from Step B above) in N,N-dimethylformamide (120 mL) was added dropwise to a cooled (−15° C.) solution of 1,1′-thiocarbonyldiimidazole (9.66 g, 54.2 mmol) (Aldrich) in N,N-dimethylformamide (40 mL). After the addition was complete, the cooling bath was removed and the solution was stirred for 1 h. The mixture was poured into ice-water (1 L), stirred for 30 minutes, and extracted with diethyl ether. The combined extracts were dried over Na2SO4, and evaporated in vacuo to provide 4-(4-isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (18 g, 94%).

Aufarbeitung

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionThe mixture was poured into ice-water (1 L)
  4. stirringstirred for 30 minutes
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66c9ae911dbb4a32a0ac6929b789a6cc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094896B2

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