Water → N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide

HRID 991416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991416
[C:1]([Br:5])(Br)(Br)Br.[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1CO)=[N:10][O:11][CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:1][Br:5])=[N:10][O:11][CH3:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Produkt 1

HCID 53790204N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Carbon tetrabromide (0.33 g) was added to a solution of N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide (0.11 g) and triphenylphosphine (0.26 g) in tetrahydrofuran (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1½ hours and then at room temperature for 1 hour. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried over magnesium sulphate. The solution was then concentrated under reduced pressure to leave a gum. Column chromatography (eluting with diethyl ether on silica gel) gave the N-methyl-2-(2-bromomethylphenyl)-2-methoxyimino-acetamide as a gum (80 mg, 57%). 1H NMR (CDCl3) δ2.95(d,3H), 4.0(s,3H), 4.35(s,2H), 6.8(brs,1H), 7.1-7.5(m,4H) ppm.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationThe solution was then concentrated under reduced pressure
  5. customto leave a gum
  6. washColumn chromatography (eluting with diethyl ether on silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-5e4a6f1e925849f286927a5d7d934790
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465457B1

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