Water → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole

HRID 322394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322394
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[O:23][CH:24]=1.O>CN(C)C=O>[N:13]1([CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:19][C:20]3[N:21]=[C:22]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[O:23][CH:24]=3)=[CH:5][CH:6]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Produkt 1

HCID 98639314-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (90 mg) was added to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (405 mg) in N,N-dimethyl formamide at room temperature and stirred for 1.5 hours. 4-Chloromethyl-2-(2-thienyl)oxazole (480 mg) was added, and the resultant was stirred at 90° C. for further 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel chromatography. From the fraction eluted with ethyl acetate-methanol (50:1, v/v), 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole (650 mg, 89%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 84-85° C.

Aufarbeitung

  1. stirringthe resultant was stirred at 90° C. for further 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-methanol (50:1

Quellen und Nachweise

ORD-Eintrag
ord-aaa20e4594354ceca64fd08ab2acc231
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

Notizen zur Reaktion

Wird geladen…