Phosgene → 4-Methylbenzimidazolone

반응식

[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

참가 물질

반응물 3

HCID 6371Phosgene

HCID 175932,3-Diaminotoluene

HCID 5250894Bis-(1H-imidazol-2-YL)-methanone

생성물 1

HCID 203602224-Methylbenzimidazolone

실험 절차

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.

출처 및 근거

ORD 기록: ord-f5bf866af74d4a07ae8ec10d49278f9c
출처 데이터셋: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05273975

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