Hydrochloric Acid → 1,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one

HRID 46843

Reaktionsgleichung

Reaktionsgleichung von HRID 46843
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][OH:16].Cl.[O-:18][C:19]#N.[K+]>O>[OH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[NH:1][C:19]1=[O:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 203855523-{[2-Amino-4-(trifluoromethyl)phenyl]amino}-1-propanol

Produkt 1

HCID 203856341,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 21 parts of 3-{[2-amino-4-(trifluoromethyl)phenyl]amino}-1-propanol and 100 parts of water are added 14.4 parts of hydrochloric acid solution. The whole is stirred for 10 minutes at room temperature. After cooling to 0°-10° C., there is added dropwise a solution of 18 parts of potassium cyanate in 50 parts of water. Upon completion, stirring is continued for 2 hours. The precipitated product is filtered off and dried. Then it is melted and the melt is stirred for 10 minutes. After cooling, it is dissolved in trichloromethane while heating. The solution is filtered and the product is allowed to crystallize from the filtrate. It is filtered off and dried, yielding 8 parts (34%) of 1,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one.

Aufarbeitung

  1. temperatureAfter cooling to 0°-10° C.
  2. stirringUpon completion, stirring
  3. waitis continued for 2 hours
  4. filtrationThe precipitated product is filtered off
  5. customdried
  6. stirringthe melt is stirred for 10 minutes
  7. temperatureAfter cooling
  8. dissolutionit is dissolved in trichloromethane
  9. temperaturewhile heating
  10. filtrationThe solution is filtered
  11. customto crystallize from the filtrate
  12. filtrationIt is filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c7824292522f4497a8640ecf1cdb2402
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

Verknüpfte Notizen

Wird geladen…