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Ethanol → 5-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 49527
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49527
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)=[O:10])#[N:2].C([OH:28])C.OO.[OH-].[Na+]>O>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=1)=[O:10])(=[O:28])[NH2:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 784Hydrogen Peroxide2×HCID 14798Sodium Hydroxide2×HCID 178305785-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

Produkt 1

HCID 120946625-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 484 mg of 5-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 10 ml of ethanol, 0.6 ml of 30% aqueous hydrogen peroxide and 5 ml of 0.1 mol/l sodium hydroxide, and the mixture was stirred for 1 hour at 50° C. Then, 0.6 ml of 30% aqueous hydrogen peroxide and 5 ml of 0.1 mol/l sodium hydroxide were added again and the mixture was stirred for 30 minutes at 50° C. The reaction mixture was poured into water and extracted with ethyl acetate. After washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence, the organic layer was dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1 to 50:1) to obtain 318 mg of 5-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes at 50° C
  2. extractionextracted with ethyl acetate
  3. washAfter washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationSolvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1 to 50:1)

Quellen und Nachweise

ORD-Eintrag
ord-35e359ae8a194026a6582d566ab31712
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06706763B1

Notizen zur Reaktion

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