Methanol → (E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 1769414

Reaktionsgleichung

Reaktionsgleichung von HRID 1769414
C[O:2][C:3](=O)/[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:5]/[OH:6].CO.[CH3:23][NH2:24].O>C1(C)C=CC=CC=1>[OH:6]/[N:5]=[C:4](\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:3]([NH:24][CH3:23])=[O:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 6329Methylamine2×HCID 88276687methyl (2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetate

Produkt 1

HCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To crude E-α-hydroxyimino-2-phenoxyphenylacetic acid methyl ester (39.6 g, 0.0747 mole, purity: 51.2%) were added methanol (100 ml) and 40% aqueous solution of methylamine (15.45 g, 0,199 mole) and the mixture was stirred at room temperature for 15 hours. Then, 40% aqueous solution of methylamine (7.73 g, 0.0995 mole) was added to the mixture which was stirred in an oil bath at 70° C. for 6 hours. After completion of the reaction, water (200 ml) and toluene (100 ml) were added to the reaction mixture, which was stirred with ice cooling for one hour. The precipitated crystals were filtered off and recrystallized (methanol/toluene) to obtain E-2-hydroxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (12.31 g, yield: 60.1%) as colorless crystals (melting point: 183°-184.5° C.).

Aufarbeitung

  1. stirringwas stirred in an oil bath at 70° C. for 6 hours
  2. additionwere added to the reaction mixture, which
  3. stirringwas stirred with ice cooling for one hour
  4. filtrationThe precipitated crystals were filtered off
  5. customrecrystallized (methanol/toluene)

Quellen und Nachweise

ORD-Eintrag
ord-b6408387a93c44e59a88ce5f1751e900
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380913

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