Triethylamine → 4-Phenylbutyl 2-[benzylsulfonyl]-perhydropyridazinecarboxylate

HRID 851941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851941
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:19])[NH:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([S:8]([N:13]1[CH:14]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:19])[CH2:15][CH2:16][CH2:17][NH:12]1)(=[O:10])=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 184700714-Phenylbutyl perhydropyridazinecarboxylate

Produkt 1

HCID 184700884-Phenylbutyl 2-[benzylsulfonyl]-perhydropyridazinecarboxylateAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of α-toluene sulfonyl chloride (1.12 g, 5.77 mmol) in CH2Cl2 was added to a CH2Cl2 solution containing 4-phenylbutyl perhydropyridazinecarboxylate (1.37 g, 5.2 mmol) and triethylamine (0.83 ml, 6 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere, and then diluted to 50 ml CH2Cl2. The organic layer was washed with water, dried, and concentrated. The crude material was purified by silica gel column to yield 1.4 g (64%) final product as clear oil. Rf=0.60 (2:1 hexane:EtOAc). 1H NMR (CDCl3, 400 MHz): δ 1.68 (m, 8H); 2.67 (m, 2H); 2.90 (m, 1H); 3.38 (m, 2H); 4.22 (m, 5H); 7.32 (m, 10H). Anal. Calcd. for C22H28N2S1O4: C, 63.44; H, 6.78; N, 6.73, S, 7.70. Found: C, 63.86; H, 6.83; N, 6.41, S, 7.58.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-0f0075878d534f4a9f0888e44873c657
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253169B2

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