Potassium Carbonate → HCID 21846932, compound

HRID 619733Notes

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:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:16]2[N:17]([CH2:21][CH3:22])[C:18]([CH3:20])=[N:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:21]([N:17]1[C:16]2[CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[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)=[CH:14][C:15]=2[N:19]=[C:18]1[CH3:20])[CH3:22]

Participants

Conditions

Temperature: 130 °C

Procedure

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 20 ml, 5-chloro-1-ethyl-2-methyl-6-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 3 hours at 130° C. The reaction mixture was concentrated under reduced pressure, the residue was crystallized with ethyl acetate, and 1-ethyl-5-(5-isoquinolylsulfanyl)-2-methyl-6-nitro-1H-benzo[d]imidazole 480 mg (42.3%) was obtained.

Workup

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

Sources & evidence

ORD record: ord-0344e0bc1d304b3ea3fe6a056152c286
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959107

Reaction notes

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