Methionin AL → 6-(3,5-Dimethylbenzyl)-5-isopropyluracil

HRID 1072965

Reaktionsgleichung

Reaktionsgleichung von HRID 1072965
N[C@H](C=[O:8])CCSC.[NH2:9][C:10]([NH2:12])=S.[CH3:13][CH:14]([CH3:32])[CH:15]([C:21](=O)[CH2:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:16](OCC)=[O:17]>C(O)C>[CH3:30][C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([CH3:29])[CH:26]=1)[CH2:22][C:21]1[NH:12][C:10](=[O:8])[NH:9][C:16](=[O:17])[C:15]=1[CH:14]([CH3:32])[CH3:13]

Komponenten

5

Edukt 3

HCID 446793Methionin ALHCID 2723790ThioureaHCID 21635576Ethyl 3-methyl-2-(3,5-dimethylphenylacetyl)butanoate

Produkt 1

HCID 107309016-(3,5-Dimethylbenzyl)-5-isopropyluracilAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Metal sodium (23.8 g, 1.034 mol) was reacted with anhydrous ethanol (500 ml). To the clear obtained solution, was added thiourea (54.35 g, 714 mmol) and ethyl 3-methyl-2(3,5-dimethylphenylacetyl)butanoate (13.14 g, 47.6 mol). The reaction medium was maintained under reflux for 6 h, and then was concentrated in vacuo at 40.50° C. To the obtained residue was added concentrated hydrochloric acid (100 ml) and then the solution was brought to pH 4 with acetic acid. The obtained 6-dimethylbenzyl-5-isopropyl-2-thiouracil was dissolved in an aqueous 10% chloroacetic acid solution (200 ml) and the solution was maintained under reflux for 24 h and then cooled to ambient temperature and the obtained precipitates were separated by filtration and washed with cold ethanol and then with ether, and then dried in vacuo at 40° C. to give 6-(3,5-dimethylbenzyl)-5-isopropyluracil (7 g, 54%). Melting point: 213-214° C.

Aufarbeitung

  1. temperatureThe reaction medium was maintained
  2. temperatureunder reflux for 6 h
  3. concentrationwas concentrated in vacuo at 40.50° C
  4. additionTo the obtained residue was added concentrated hydrochloric acid (100 ml)
  5. dissolutionThe obtained 6-dimethylbenzyl-5-isopropyl-2-thiouracil was dissolved in an aqueous 10% chloroacetic acid solution (200 ml)
  6. temperaturethe solution was maintained
  7. temperatureunder reflux for 24 h
  8. customthe obtained precipitates
  9. customwere separated by filtration
  10. washwashed with cold ethanol
  11. dry with materialwith ether, and then dried in vacuo at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-cb0ad1968cf54acca043b32b31b7d52f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911450B1

Verknüpfte Notizen

Wird geladen…