Dimethylformamide → methyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazole-5-carboxylate

HRID 1295268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295268
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.Cl[CH2:18][C:19]1[CH:37]=[CH:36][C:22]([O:23][CH2:24][C:25]2[N:26]=[C:27]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)[O:28][C:29]=2[CH3:30])=[C:21]([O:38][CH3:39])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:32]1[CH:33]=[CH:34][CH:35]=[C:31]1[C:27]1[O:28][C:29]([CH3:30])=[C:25]([CH2:24][O:23][C:22]2[CH:36]=[CH:37][C:19]([CH2:18][O:1][C:2]3[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:3]=3)=[CH:20][C:21]=2[O:38][CH3:39])[N:26]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazoleHCID 178498600HCID 178498600, Verbindung

Produkt 1

HCID 69434415methyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazole-5-carboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of methyl 3-hydroxy-1-phenyl-1H-pyrazole-5-carboxylate (5.60 g), 4-(4-chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole (9.45 g), potassium carbonate (3.55 g) and N,N-dimethylformamide (200 ml) was stirred at 90° C. for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were collected by filtration to give methyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazole-5-carboxylate (12.40 g, yield 94%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 146–147° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained colorless crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f91b1ab40e0f4a2fb26495bdd4eab5e6
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241785B2

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