Phosgene → 4-Methylbenzimidazolone

HRID 1648275Notes

Reaction equation

HRID 1648275 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 203602224-Methylbenzimidazolone

Procedure

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-bromo-succinimine to give compound XXXIX. This is coupled with VIIb and the resulting adduct LX is hydrolyzed to LI. Reduction with lithium aluminum hydride alcohol LXlI which was treated with carbon tetrabromide/triphenylphosphine to give compound 51. Compound 51 was refluxed in acetic acid to effect conversion to compound 6.

Sources & evidence

ORD record
ord-4ab0edc23221454e93064f71cec97a4f
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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