Isopropanol → HCID 131723675, Verbindung

HRID 2297391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2297391
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27](=[O:35])[NH:28][C:29]2[NH:30][CH2:31][CH2:32][CH2:33][N:34]=2)=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:38])=O.[CH:40](O)([CH3:42])[CH3:41]>>[ClH:38].[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27](=[O:35])[NH:28][C:29]2[NH:34][CH2:33][CH2:32][CH2:31][N:30]=2)=[CH:19][CH:18]=1)[C:13]([O:15][CH:40]([CH3:42])[CH3:41])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 3776Isopropanol3×HCID 24386Thionyl Chloride2×HCID 11540287HCID 11540287, Verbindung

Produkt 1

HCID 131723675HCID 131723675, Verbindung

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

23.88 g (0.04 mol) of the compound of Example 1 (as trifluoroacetic acid salt) were suspended in 400 ml of isopropanol. To this suspension was added at −15° C. under an inert gas atmosphere a previously prepared solution of thionyl chloride in isopropanol (for the preparation of this solution 10.4 ml of thionyl chloride had been added dropwise at −10 to −15° C. and unter an inert gas atmosphere within 5 min to 160 ml of isopropanol and the mixture had been stirred at −10° C. for further 20 min). After completion of the addition the temperature rose within 30 min to room temperature. Then, the meanwhile clear solution was heated at 60° C. under stirring for 7 hours. Stirring was continued without heating overnight. By TLC control, the reaction exhibited to be completed. Solvents were removed by rotary destination in vacuo. The residue was suspended in 100 ml of isopropanol and the isopropanol was removed in vacuo. The solid residue was triturated with diethylether and separated by suction filtration. The raw product was suspended in 120 ml of isopropanol, heated to reflux with 2.4 g of charcoal and filtered. After cooling, the colourless product was separated by filtration. Yield: 16.2 g of an off-white solid.

Aufarbeitung

  1. additionhad been added dropwise at −10 to −15° C.
  2. additionAfter completion of the addition the temperature
  3. temperatureThen, the meanwhile clear solution was heated at 60° C.
  4. stirringunder stirring for 7 hours
  5. stirringStirring
  6. temperaturewithout heating overnight
  7. customSolvents were removed by rotary destination in vacuo
  8. customthe isopropanol was removed in vacuo
  9. customThe solid residue was triturated with diethylether
  10. customseparated by suction filtration
  11. temperatureheated
  12. temperatureto reflux with 2.4 g of charcoal
  13. filtrationfiltered
  14. temperatureAfter cooling
  15. customthe colourless product was separated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-07e1810638bc4986af0a4f24da772c46
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492356B1

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