4-Methoxyphenol → 4-Bromomethyl-7-acetoxycoumarin

HRID 1603178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603178
[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14](=[O:16])[CH3:15])=[CH:10][CH:11]=2)[O:6][C:5](=[O:17])[CH:4]=1.CNN(NC)C(=O)C(C)=CCCC.COC1C=CC(O)=CC=1.[CH3:40][N:41]([CH2:43][CH2:44][CH2:45][CH:46]=[C:47]([CH3:51])[C:48]([NH2:50])=[O:49])[CH3:42].CC(C)=O>CC(C)=O>[CH3:40][N:41]([CH2:43][CH2:44][CH2:45][CH:46]=[C:47]([CH3:51])[C:48]([NH2:50])=[O:49])[CH3:42].[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14](=[O:16])[CH3:15])=[CH:10][CH:11]=2)[O:6][C:5](=[O:17])[CH:4]=1

Komponenten

7

Edukt 4

HCID 90154-MethoxyphenolHCID 1882964-Bromomethyl-7-acetoxycoumarin2×HCID 129711983n,n-DimethylaminopropylmethacrylamideHCID 131721451DMAPMA acetone

Produkt 2

HCID 1882964-Bromomethyl-7-acetoxycoumarinHCID 20976834Dimethylaminopropylmethacrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A quaternary ammonium salt of dimethylaminopropylmethacrylamide (DMAPMA) and 4-(bromomethyl)-7-acetoxycoumarin was synthesized in the following manner. One gram of 4-(bromomethyl)-7-acetoxycoumarin (available from TCI America; Portland, Oreg.), (3.36 mmol) was charged to a 100 mL round bottom flask equipped with a magnetic stir bar and a reflux condenser. Enough acetone (reagent grade or better) to dissolve the material at reflux was added (about 40 mL). N,N-Dimethylaminopropylmethacrylamide (DMAPMA, available from Rohm Tech. Inc.; Malden, Mass.), 1.43 g (2.5 equivalents) was dissolved in about 10 mL of acetone. 4-Methoxyphenol (available from Aldrich; Milwaukee, Wis.), 20 mg, was added to the DMAPMA/acetone solution, and this solution was added dropwise to the 4-(bromomethyl)-7-acetoxycoumarin using an addition funnel over the course of about 10 minutes. The reaction mixture was maintained at reflux for 2 hours, after which time the solution was allowed to cool to room temperature. Left to stand overnight, the product crystallized from the reaction mixture to form a fine white powder that was easily collected by filtration (1.53 g), and characterized by NMR.

Aufarbeitung

  1. customequipped with a magnetic stir bar and a reflux condenser
  2. temperatureat reflux
  3. additionwas added (about 40 mL)
  4. temperatureThe reaction mixture was maintained
  5. temperatureat reflux for 2 hours
  6. waitLeft
  7. customthe product crystallized from the reaction mixture
  8. customto form a fine white powder that
  9. filtrationwas easily collected by filtration (1.53 g)

Quellen und Nachweise

ORD-Eintrag
ord-97741d3161924893ba0a1549ca23248f
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986030

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