Pyridine → N'-[4-(4-isopropylphenethyloxy)phenyl]-N-methoxy-N-methylurea

HRID 65820

Reaktionsgleichung

Reaktionsgleichung von HRID 65820
[CH:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](Cl)=[O:19])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:29][NH:30][O:31][CH3:32]>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:19])[N:30]([O:31][CH3:32])[CH3:29])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 14232N,O-DimethylhydroxylamineHCID 227559994-(4-Isopropylphenethyloxy)phenylcarbamyl chloride

Produkt 1

HCID 22756003N'-[4-(4-isopropylphenethyloxy)phenyl]-N-methoxy-N-methylureaAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Into a solution of 10.6 g of 4-(4-isopropylphenethyloxy)phenylcarbamyl chloride in 200 ml of toluene are added 4 ml of pyridine and a solution of 2.5 g of N,O-dimethylhydroxylamine in 50 ml of toluene at a temperature below 20° C. The mixture is heated under reflux for 4 hours. The reaction mixture is then poured into ice water, and the separated organic layer is washed with dilute hydrochloric acid, thoroughly washed with water and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure, and the crude crystals are recrystallized from ethanol to obtain 4.8 g of N'-[4-(4-isopropylphenethyloxy)phenyl]-N-methoxy-N-methylurea as white needles, M.P. 81°-82° C.

Aufarbeitung

  1. customat a temperature below 20° C
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 4 hours
  4. washthe separated organic layer is washed with dilute hydrochloric acid
  5. washthoroughly washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe crude crystals are recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ab87deb8c12c442892eeaba8a286c718
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04129436

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