Allyl bromide → 3-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl ester

HRID 1977354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977354
[CH2:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([C:15](=[O:19])[N:16]([OH:18])[CH3:17])[CH:7]=1)[CH:2]=[CH2:3].[CH2:21](Br)[CH:22]=[CH2:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([C:15](=[O:19])[N:16]([O:18][CH2:23][CH:22]=[CH2:21])[CH3:17])[CH:7]=1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 229861013-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl ester

Produkt 1

HCID 229861003-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl esterAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (8(a)) (0.60 g), allyl bromide (0.28 g), potassium carbonate (0.59 g) and DMF (20 ml) was stirred for 3 hours at ambient temperature under an argon atmosphere. The dimethyl formamide was then evaporated under reduced pressure and the residue dissolved in ethyl acetate (50 ml) and water (50 ml). The organic phase was separated, washed with brine (50 ml), dried over magnesium sulphate and evaporated under reduced pressure to dryness to give 3-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl ester (8(b)) as a yellow oil (0.571 g).

Aufarbeitung

  1. customThe dimethyl formamide was then evaporated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure to dryness

Quellen und Nachweise

ORD-Eintrag
ord-793cee6126f848ceb335d8fb4c0a33b6
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232338B1

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