StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisopropylethylamine → HCID 178478954, Verbindung

HRID 2223829
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2223829
C([N:20]1[CH:24]=[C:23]([CH2:25][NH2:26])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[N:42]=[C:41]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[N:40]=[C:39]([NH:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[N:38]=1.C(OC(=O)C)C.Cl>C(#N)C.C(O)(=O)C.C(OCC)(=O)C.O>[ClH:36].[F:50][C:47]1[CH:46]=[CH:45][C:44]([NH:43][C:41]2[N:42]=[C:37]([NH:26][CH2:25][C:23]3[N:22]=[CH:21][NH:20][CH:24]=3)[N:38]=[C:39]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:40]=2)=[CH:49][CH:48]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 230331686-Chloro-N~2~-(4-fluorophenyl)-N~4~-phenyl-1,3,5-triazine-2,4-diamineHCID 23033177(1-Trityl-1H-imidazol-4-yl)methanamine

Produkt 1

HCID 178478954HCID 178478954, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel2×
HCID 6342AcetonitrileLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 678 mg portion of [(1-trityl-1H-imidazol-4-yl)methyl]amine was dissolved in 10.0 ml of acetonitrile, and 0.52 ml of diisopropylethylamine and 316 mg of the 6-chloro-N-(4-fluorophenyl)-N′-phenyl-1,3,5-triazine-2,4-diamine synthesized in Reference Example 1 were added thereto and stirred at 80° C. for 3 days. After cooling down to room temperature, the reaction solution was mixed with water and extracted with ethyl acetate. The organic layer was washed with citric acid aqueous solution and saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (99:1) to obtain a crude product. This crude product was dissolved in 9 ml of acetic acid and 1 ml of water and stirred at 70° C. for 2 hours. After evaporation of the reaction solution under a reduced pressure, the residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (90:10) to obtain a crude product. This crued product was dissolved in ethyl acetate and mixed with 4 M hydrochloric acid ethyl acetate solution, and the thus formed crystals were collected by filtration and dried to obtain 306 mg of N-(4-fluorophenyl)-N′-(1H-imidazol-4-ylmethyl)-N″-phenyl-1,3,5-triazine-2,4,6-triamine hydrochloride as colorless crystals.

Aufarbeitung

  1. additionwere added
  2. temperatureAfter cooling down to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with citric acid aqueous solution and saturated brine
  5. customdried
  6. customThe solvent was evaporated under a reduced pressure
  7. washeluted with chloroform:methanol (99:1)
  8. customto obtain a crude product
  9. customAfter evaporation of the reaction solution under a reduced pressure
  10. additionthe residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with saturated brine
  13. customdried
  14. customThe solvent was evaporated under a reduced pressure
  15. washeluted with chloroform:methanol (90:10)
  16. customto obtain a crude product
  17. filtrationthe thus formed crystals were collected by filtration
  18. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0e884dc45de24d5aaf23fb4316ebc00b
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07375222B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion