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Hydrochloric Acid → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamide

HRID 742425
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 742425
Br.[NH2:2][CH2:3][CH2:4][Br:5].[C:6](=O)([O-])[O-:7].[K+].[K+].[F:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][C:14]=1[N:26]1C(=O)[CH:30]2[CH2:33][CH2:34][CH2:35][C:28](=[CH:29]2)[C:27]1=[O:36].Cl>C(#N)C>[F:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][C:14]=1[NH:26][C:27](=[O:36])[C:28]1[CH2:35][CH2:34][CH2:33][CH2:30][C:29]=1[C:6]([NH:2][CH2:3][CH2:4][Br:5])=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27742172-Bromoethylamine hydrobromideHCID 19425191N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide

Produkt 1

HCID 19425254N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamideAusbeute 165,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Aminoethyl bromide hydrobromide (0.280 g, 1.37 mmol) and potassium carbonate (0.110 g, 0.796 mmol) were placed into a round bottom flask (25 cc), followed by stirring at room temperature in an acetonitrile solvent until the generation of gas ceased. Then, N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (0.500 g, 1.37 mmol) was added thereto, followed by stirring for 30 minutes at room temperature. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (20 ml), and the mixture was extracted with ethyl acetate (30 ml×3 portions). After drying the organic layer over anhydrous magnesium sulfate, the drying agent was removed, and the solvent was distilled off under reduced pressure. The precipitated crystals were isolated by filtration, washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.644 g, 96.4% yield).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (30 ml×3 portions)
  3. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  4. customthe drying agent was removed
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe precipitated crystals were isolated by filtration
  7. washwashed with hexane
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5c7b4eaaa928438cbdd254739384f623
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05554581

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