Potassium Carbonate → 1-ethyl-6-(5-isoquinolylsulfanyl)-2-methyl-5-nitro-1H-benzo[d]imidazole

HRID 619731

Reaction equation

[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([SH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.Cl[C:13]1[C:14]([N+:25]([O-:27])=[O:26])=[CH:15][C:16]2[N:20]=[C:19]([CH3:21])[N:18]([CH2:22][CH3:23])[C:17]=2[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:22]([N:18]1[C:17]2[CH:24]=[C:13]([S:11][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)[C:14]([N+:25]([O-:27])=[O:26])=[CH:15][C:16]=2[N:20]=[C:19]1[CH3:21])[CH3:23]

Participants

Conditions

Temperature: 130 °C

Procedure

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 20 ml, 6-chloro-1-ethyl-2-methyl-5-nitro-1H-benzo[d]imidazole 910 mg (3.1 mmol) and potassium carbonate 1.29 g (9.3 mmol) were added, and the mixture was stirred for 6 hours at 130° C. The reaction mixture was concentrated under reduced pressure, the residue was crystallized with ethyl acetate, and 1-ethyl-6-(5-isoquinolylsulfanyl)-2-methyl-5-nitro-1H-benzo[d]imidazole 410 mg (35.8%) was obtained.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was crystallized with ethyl acetate

Sources & evidence

ORD record: ord-419f836f31444b5ea88aa33c5bb92832
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959107

Linked notes

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