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Triethylamine → HCID 67618000, Verbindung

HRID 1451205
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1451205
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14].I.[CH3:20][N:21]([CH3:26])[C:22](=N)[S:23][CH3:24].C([N:29](CC)CC)C>O1CCCC1>[CH3:24][S:23][CH2:22][N:21]([CH:26]=[N:29][S:13]([NH:16][C:17]([NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1)=[O:18])(=[O:15])=[O:14])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 12762363Methyl N,N-dimethylcarbamimidothioate--hydrogen iodide (1/1)

Produkt 1

HCID 67618000HCID 67618000, VerbindungAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was dropwise added thereto in a range of from -20° C. to -15° C. The reaction temperature was raised to 0° C., and the mixture was cooled again to -20° C. Then, a mixture comprising 2.5 g (10.2 mmol) of N,N-dimethyl-S-methylisothiourea hydroiodide, 2.22 g (22 mmol) of triethylamine and 30 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 10 minutes. Then, the solvent was distilled off under reduced pressure, and then 80 ml of water was added to the obtained residue. The mixture was extracted three times with 30 ml of chloroform. The chloroform layer was washed with water and then dried over anhydrous sodium sulfate. Then, solvent was distilled off under reduced pressure. Obtained crystals were washed with a solvent mixture of ethyl ether/ acetonitrile to obtain 2 g of desired 1-[N-((methylthio-N,N-dimethylamino)methylene)aminosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea. Melting point: 167°-168° C.

Aufarbeitung

  1. customof from -20° C. to -15° C
  2. temperaturethe mixture was cooled again to -20° C
  3. temperatureThe reaction temperature was raised to room temperature
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. addition80 ml of water was added to the obtained residue
  6. extractionThe mixture was extracted three times with 30 ml of chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThen, solvent was distilled off under reduced pressure
  10. customObtained crystals
  11. washwere washed with a solvent mixture of ethyl ether/ acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-19678e3b0b674150a201921bf790345d
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05604179

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