Hydrochloric Acid → HCID 68886240, Verbindung

HRID 1294352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294352
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][C:9](N(C)C)=O.C[O-].[Na+].ClC[C:24]1[CH:25]=[C:26]([CH:41]=[CH:42][CH:43]=1)[O:27][CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][C:42]1[CH:43]=[CH:24][CH:25]=[C:26]([O:27][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])[CH:41]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 10942334Sodium MethoxideHCID 15840683HCID 15840683, Verbindung

Produkt 1

HCID 68886240HCID 68886240, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A mixture of methyl [3-chloro-4-[(dimethylamino)carbonylthio]phenyl]acetate (0.80 g), a 28% solution of sodium methoxide in methanol (0.75 g) and methanol (20 mL) was stirred with heating under reflux for 2 hrs. 4-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.87 g) was added to the reaction mixture at room temperature and the mixture was further stirred for 12 hrs. The reaction mixture was poured into 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-[3-chloro-4-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetate as a colorless oil (0.48 g, yield 35%), from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1b84e7f910d4f018c0036905cfd87c4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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