Phosgene → 4-Methylbenzimidazolone

HRID 327431

Reaktionsgleichung

Reaktionsgleichung von HRID 327431
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10](C1NC=CN=1)(C1NC=CN=1)=[O:11].C(Cl)(Cl)=O>>[CH3:1][C:2]1[C:3]2[C:4](=[N:8][C:10](=[O:11])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 6371PhosgeneHCID 175932,3-DiaminotolueneHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Produkt 1

HCID 203602224-Methylbenzimidazolone

Versuchsvorschrift

The 5-amino-5,6-dihydro-4H-imidazo(4,5,1-ij)quinolin-2-ones of the invention may also be prepared by the route shown in Scheme 6. 3-Methyl-1,2-benzenediamine is reacted with carbonyl diimidazole or phosgene to give 4-methylbenzimidazolone (XXXVI). This is refluxed with phosphorus oxychloride to give XXXVII which is protected and reacted with N-bromosuccinimine to give compound XXXIX. This is coupled with VIIb and the resulting adduct LX is hydrolyzed to LI. Reduction with lithium aluminum hydride alcohol LXII which was treated with carbon tetrabromide/triphenylphosphine to give compound 51. Compound 51 was refluxed in acetic acid to effect conversion to compound 6.

Quellen und Nachweise

ORD-Eintrag
ord-f5bf866af74d4a07ae8ec10d49278f9c
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273975

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