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

HRID 1684364노트

반응식

HRID 1684364 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea58a005bce443b59f27aaff0ecf1a10
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639887

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