Methane → HCID 54024057, Verbindung

HRID 1448094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448094
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17](N)[C:18](NC)=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:30][C:31]([NH2:33])=[O:32].[CH4:34]>O.Cl>[C:24]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]4[N:30]([CH3:34])[C:31](=[O:32])[NH:33][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 297MethaneHCID 1176UreaHCID 30178794-{[4-(Diphenylmethyl)piperazin-1-yl]methyl}-N~1~-methylbenzene-1,2-diamine

Produkt 1

HCID 54024057HCID 54024057, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of 4.64 parts of 4-[4-(diphenylmethyl)-1-piperazinylmethyl]-N1 -methyl-1,2-benzenediamine and 1.2 parts of urea is stirred and heated for 1.50 hours at 190° C. The reaction mixture is cooled and dissolved in a mixture of 150 parts of water and 6 parts of a hydrochloric acid solution 10 N. The solution is treated with activated charcoal. The latter is filtered off and the filtrate is alkalized with a sodium hydroxide solution 5 N. The product is extracted three times with dichloromethane. The combined extracts are dried, filtered and evaporated. The solid residue is stirred in 20 parts of ethanol. The product is filtered off and purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is treated with 20 parts of ethanol. The product is filtered off, washed with a small amount of ethanol and dried, yielding 1.7 parts of 5- [4-(diphenylmethyl)-1-piperazinylmethyl]-1,3-dihydro-1-methyl-2H-benzimidazol-2-one; mp. 246° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe latter is filtered off
  3. extractionThe product is extracted three times with dichloromethane
  4. customThe combined extracts are dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe solid residue is stirred in 20 parts of ethanol
  8. filtrationThe product is filtered off
  9. custompurified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. additionThe solid residue is treated with 20 parts of ethanol
  14. filtrationThe product is filtered off
  15. washwashed with a small amount of ethanol
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7db400e3ebc04d23be720270fe5dfb7b
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179505

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