Sodium Hydroxide → alpha-(3,4-Dimethoxyphenyl)-1,3-dihydro-5,6-dimethoxy-alpha-[(4-methylphenyl)thio]-2H-isoindole-2-heptanenitrile

HRID 1684364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684364
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[C:31]=1CCl.[OH-].[Na+].[C:44](=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:7]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]2[CH2:29][C:30]3[C:35](=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)[CH2:44]2)[C:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10572107alpha-(5-Aminopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileHCID 153389181,2-Bis(chloromethyl)-3,4-dimethoxybenzene

Produkt 1

HCID 10745170alpha-(3,4-Dimethoxyphenyl)-1,3-dihydro-5,6-dimethoxy-alpha-[(4-methylphenyl)thio]-2H-isoindole-2-heptanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 3.03 g of α-(5-aminopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile, 1.85 g of 1,2-bis(chloromethyl)-3,4-dimethoxybenzene, 20 mL of toluene, and 0.22 g of tetrabutylammonium chloride, is added water containing 2 g of sodium hydroxide. The mixture is stirred for 48 hours. Upon adjusting the pH of the aqueous layer to pH 9 with solid sodium bicarbonate, the layers are separated and the aqueous layer further extracted with chloroform. After drying the combined organic extracts over sodium sulfate, they are passed through a pad of hydrous magnesium silicate, and concentrated in vacuo to a brown gum. This gum is purified by HPLC using a reverse phase C-18 radial-pak column (6 cm.×30 cm.) with a buffered solvent system (150 mL ammonium hydroxide in water adjusted to a pH 4.00 with acetic acid, then diluted to 7,875 mL with water; 5700 mL of acetonitrile and 1425 mL of methyl alcohol are added). After solvent removal, 0.85 g of the desired product is obtained as a yellow oil.

Aufarbeitung

  1. customthe layers are separated
  2. extractionthe aqueous layer further extracted with chloroform
  3. dry with materialAfter drying the combined organic extracts over sodium sulfate, they
  4. concentrationconcentrated in vacuo to a brown gum
  5. customThis gum is purified by HPLC
  6. additiondiluted to 7,875 mL with water
  7. addition5700 mL of acetonitrile and 1425 mL of methyl alcohol are added)
  8. customAfter solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-ea58a005bce443b59f27aaff0ecf1a10
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639887

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