Benzoyl chloride → 1-Benzoyl-1,3-dicyclohexyl-O-(N-2-butylideneamino)-isourea

HRID 2275477

Reaktionsgleichung

Reaktionsgleichung von HRID 2275477
[CH:1]1([NH:7][C:8](=[N:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:9][N:10]=[C:11]([CH2:13][CH3:14])[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C1C=CN=CC=1.ClCCl.CCCCCC>[C:29]([N:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:8](=[N:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[O:9][N:10]=[C:11]([CH2:13][CH3:14])[CH3:12])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

7

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 866646331,3-Dicyclohexyl-O-(N-2-butylideneamino)-isourea

Produkt 1

HCID 866646401-Benzoyl-1,3-dicyclohexyl-O-(N-2-butylideneamino)-isoureaAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 1,3-dicyclohexyl-O—(N-2-butylideneamino)-isourea (Cmpd. 2) (7.34 g, 25 mmol) and 4-dimethylaminopyridine (100 mg) in dichloromethane (25 ml) and triethylamine (3.9 ml, 27.5 mmol) is added benzoyl chloride (3.58 g, 25.5 mmol). The mixture is stirred 6 h at room temperature, diluted with hexane (200 ml), washed with water (4×20 ml), dried over MgSO4 and evaporated. The residue is chromatographed on silica gel (hexanes-ethyl acetate 4:1) and the pure fractions are recrystallized from hexane to afford 7.2 g of the title compound as white crystals, mp 74-78° C.

Aufarbeitung

  1. washwashed with water (4×20 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue is chromatographed on silica gel (hexanes-ethyl acetate 4:1)
  5. customthe pure fractions are recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-818767914b55479cbb6a79bd266b4120
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09127098B2

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