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

HRID 1585815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585815
[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 11/2 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-methoxyiminoacetamide as a gum (80 mg, 57%). 1H NMR (CDCl3) δ 2.95(d,3H), 4.0(s,3H), 4.35(s,2H), 6.8(brs,1H), 7.1-7.5(m,4H) ppm.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-07eecb609eca4c209dea6d902439d0f7
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939563

Notizen zur Reaktion

Wird geladen…