Sulfuric Acid → 4-Amino-3,5-dimethoxybenzaldehyde

HRID 867607

Reaktionsgleichung

Reaktionsgleichung von HRID 867607
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]2([OH:24])C(=O)NC(=O)NC2=O)=[CH:9][C:8]=1[O:25][CH3:26]>O>[NH2:6][C:7]1[C:8]([O:25][CH3:26])=[CH:9][C:10]([CH:15]=[O:24])=[CH:11][C:12]=1[O:13][CH3:14]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 212902805-(4-Amino-3,5-dimethoxyphenyl)-5-hydroxybarbituric acid

Produkt 1

HCID 200429634-Amino-3,5-dimethoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

28 ml of sulfuric acid (d=1.8; 0.45 mol) were heated to 120° while stirring and treated in one portion with 11.25 g of 5-(4-amino-3,5-dimethoxyphenyl)-5-hydroxybarbituric acid (0.038 mol). The mixture was stirred until evolution of gas was no longer observed (about 15-20 minutes) and then poured into a mixture of 140 g of ice and 140 g of water while stirring. Resinous polymerization products were separated by a filtration over a pad of 15 g of celite. While stirring and cooling, the filtrate was treated with 63.6 g of potassium carbonate powder until neutral. The aqueous suspension was extracted three times with 50 ml of ethyl acetate each time, the combined organic phases were dried over sodium sulfate and concentrated in water-jet vacuum. The residue was dried up to constant weight in a high vacuum. There was obtained 6.36 of crude 4-amino-3,5-dimethoxybenzaldehyde as a yellow oil which solidified on standing (mp=94°-96° C.). The purity determined by gas chromatography was 96%. 4-amino-3,5-dimethoxybenzaldehyde was converted into 2,4diamino-5-(4-amino-3,5-dimethoxybenzyl)pyrimidine as follows:

Aufarbeitung

  1. stirringThe mixture was stirred until evolution of gas
  2. custom(about 15-20 minutes)
  3. stirringwhile stirring
  4. customResinous polymerization products
  5. customwere separated by a filtration over a pad of 15 g of celite
  6. stirringWhile stirring
  7. temperaturecooling
  8. additionthe filtrate was treated with 63.6 g of potassium carbonate powder until neutral
  9. extractionThe aqueous suspension was extracted three times with 50 ml of ethyl acetate each time
  10. dry with materialthe combined organic phases were dried over sodium sulfate
  11. concentrationconcentrated in water-jet vacuum
  12. customThe residue was dried up to constant weight in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-608b0e4ca43044a39a3be6b4e069cdc3
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775756

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