Triethylamine → 4-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylate

HRID 851942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851942
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[NH:11]1.C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([NH:7][C:8]([N:11]2[CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:17])[CH2:13][CH2:14][CH2:15][NH:10]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 184700714-Phenylbutyl perhydropyridazinecarboxylate

Produkt 1

HCID 184700744-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylateAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Cyclohexylisocyanate (0.38 g, 3.0 mmol) was added to a CH2Cl2 solution containing 4-phenylbutyl perhydropyridazinecarboxylate (0.72 g, 2.75 mmol) and triethylamine (0.42 ml, 3 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 0.95 g (89%) final product as clear oil. Rf=0.28 (2:1 hexane:EtOAc). 1H NMR (CDCl3, 400 MHz): δ 1.10 (m, 3H); 1.33 (m, 3H); 1.69 (m, 10H); 1.88 (m, 2H); 2.62 (m, 2H); 2.72 (m, 1H); 2.87 (m, 1H); 3.60 (m, 1H); 4.13 (m, 3H); 4.38 (m, 1H); 5.11 (d, 1H, J=8.3); 7.23 (m, 5H). Anal. Calcd. for C22H28N3O3-0.14H2O: C, 67.75; H, 8.60; N, 10.77. Found: C, 67.75; H, 8.45; N, 10.90.

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-6a403b07fb864c96afab426ab9fad963
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253169B2

Notizen zur Reaktion

Wird geladen…