Tetrahydrofuran → 3-(2-Bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

HRID 2290784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290784
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.C(N(CC)CC)C.C1COCC1.[Br:35][CH:36]([CH3:40])[C:37](Br)=[O:38]>O>[Br:35][CH:36]([CH3:40])[C:37]([NH:1][CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1)=[O:38]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 20230261HCID 20230261, Verbindung

Produkt 1

HCID 136909903-(2-Bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazoleAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 4.13 g of 3-aminomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, 1.56 g of triethylamine and 60 ml of THF was added dropwise with stirring 3.3 g of α-bromopropionyl bromide at 0°-5° C. After stirring for 1 hour at room temperature, the reaction mixture was diluted with water and extracted with benzene. The organic phase was successively washed with sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene-ethyl acetate (5:1, v/v). Crystallization of the clean fractions from diisopropyl ether yielded 4.88 g of 3-(2-bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as colorless needles, m.p. 98°-99° C.

Aufarbeitung

  1. additionwas added dropwise
  2. extractionextracted with benzene
  3. washThe organic phase was successively washed with sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed over silica gel
  7. customCrystallization of the clean fractions from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-dbfd762b4eb64c0f9fa94a64c372c465
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618617

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