Water → 1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-3,5-dimethyl-piperazine

HRID 907526

Reaktionsgleichung

Reaktionsgleichung von HRID 907526
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[NH:3]1.[Cl:9][C:10]1[C:14](Cl)=[N:13][S:12][N:11]=1.O>CN(C=O)C>[Cl:9][C:10]1[C:14]([N:6]2[CH2:5][CH:4]([CH3:8])[NH:3][CH:2]([CH3:1])[CH2:7]2)=[N:13][S:12][N:11]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 660562,6-DimethylpiperazineHCID 798043,4-Dichloro-1,2,5-thiadiazole

Produkt 1

HCID 590139491-(4-Chloro-[1,2,5]thiadiazol-3-yl)-3,5-dimethyl-piperazineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2,6-Dimethyl-piperazine (8.1 g, 71 mmol) was heated to 100° C. in DMF (8.0 ml). 3,4-Dichloro-1,2,5-thiadiazole (3.3 ml, 35 mmol) was added and the mixture stirred at 100° C. for 3-4 h. The reaction mixture was poured into H2O and extracted with EtOAc (4×). The combined EtOAc extractions were washed with sat'd NaHCO3 (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give 7.9 g (97%) of 1-(4-chloro-[1,2,5]thiadiazol-3-yl)-3,5-dimethyl-piperazine which was used without further purification. 1H NMR (CDCl3) 3.90-3.86 (m, 2H), 3.05 (m, 2H), 2.52 (m, 2H), 1.12 (d, 6H) ppm. LC-MS (MH+)=233.

Aufarbeitung

  1. extractionextracted with EtOAc (4×)
  2. extractionThe combined EtOAc extractions
  3. washwere washed with sat'd NaHCO3 (1×), sat'd NaCl (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3ea7e018ba6f4de69e625dffc4e04115
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013156B2

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