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Tetrahydrofuran → 1-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

HRID 2293044
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2293044
[N-:1]=[C:2]=S.[NH2:4][C:5]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[N:6]=1.Cl[S:16]([N:19]=C=O)(=[O:18])=[O:17].[CH3:22][N:23]1[CH2:27][C:26](=[O:28])[N:25]([CH2:29][CH2:30][CH3:31])[C:24]1=N.C(N(CC)CC)C.[O:40]1CCCC1>>[CH3:22][N:23]1[CH2:27][C:26](=[O:28])[N:25]([CH2:29][CH2:30][CH3:31])[CH:24]1[S:16]([N:19]=[N:1][C:2]([NH:4][C:5]1[N:6]=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)=[O:40])(=[O:17])=[O:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 6

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 542389381-Methyl-3-n-propyl-2-iminoimidazolidin-4-oneHCID 178418790HCID 178418790, Verbindung

Produkt 1

HCID 53752794
1-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.16 9 (7.5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran, and 1.07 g (7.5 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at -40° C. The reaction temperature was raised to 0° C., and then the reaction mixture was cooled again to -40° C. Then, a mixture comprising 1.16 g (7.5 mmol) of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one, 0.83 g (8.2 mmol) of triethylamine and 20 ml of dry tetrahydrofuran, was added thereto. The reaction temperature was raised to room temperature, and the mixture was further stirred at the same temperature for 2 hours. Then, the solvent was distilled off under reduced pressure, and then 100 ml of water was added to the obtained residue. The mixture was extracted three times with 100 ml of chloroform. Then, the chloroform layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and precipitated crystals were washed with a solvent mixture of ethyl ether/acetonitrile and collected by filtration to obtain 0.16 g of desired 1-(1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxypyrimidin-2-yl)urea.

Aufarbeitung

  1. customat -40° C
  2. temperaturethe reaction mixture was cooled again to -40° C
  3. temperatureThe reaction temperature was raised to room temperature
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. addition100 ml of water was added to the obtained residue
  6. extractionThe mixture was extracted three times with 100 ml of chloroform
  7. washThen, the chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customprecipitated crystals
  11. washwere washed with a solvent mixture of ethyl ether/acetonitrile
  12. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-799ecca7cff14e12b6f6bb643020ac6f
Quelldatensatz
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05686390

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