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

HRID 1263606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263606
[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 (50ml). 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-c23a47d36c474d0996dc1485abe2d332
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541491B1

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