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Benzyl Bromide → 4-(2,5-Dioxo 4,4-dimethyl 3-(4-phenylmethoxy-butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

HRID 355595
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 355595
[H-].[Na+].[CH3:3][C:4]1([CH3:28])[C:8](=[O:9])[N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[C:6](=[O:22])[N:5]1[CH2:23][CH2:24][CH2:25][CH2:26][OH:27].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.P(O)(O)([O-])=O.[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:22]=[C:6]1[N:5]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]([CH3:28])([CH3:3])[C:8](=[O:9])[N:7]1[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:19])([F:20])[F:21])[CH:11]=1
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Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1329814-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrileHCID 516951Monobasic potassium phosphate

Produkt 1

HCID 221169094-(2,5-Dioxo 4,4-dimethyl 3-(4-phenylmethoxy-butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

48 mg of sodium hydride were added in several lots to 370 mg of the product of Example 58 in solution in 4 ml of dimethylformamide and the mixture was stirred for 30 minutes. Then, 0.12 ml of benzyl bromide and 40 mg of tetrabutylammonium iodide were added and after 90 minutes of reaction, the same amount of each reagent was added. The mixture was stirred for one hour and the reaction medium was poured into an ice-cooled aqueous solution of monopotassium phosphate. Extraction was carried out with ether and the extracts were washed with water and dried. The solvent was eliminated under reduced pressure and the residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1) to obtain 140 mg of the expected product melting at 75°-76° C.

Aufarbeitung

  1. additionthe same amount of each reagent was added
  2. stirringThe mixture was stirred for one hour
  3. extractionExtraction
  4. washthe extracts were washed with water
  5. customdried
  6. customthe residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1)

Quellen und Nachweise

ORD-Eintrag
ord-888980a7582d4f20aa82bd95658c2190
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE035956

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