Hydrochloric Acid → HCID 9973454, compound

HRID 1974482Notes

Reaction equation

HRID 1974482 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[C:6](=[O:16])[NH:5]2.[OH-].[K+].[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][CH:20]=1.Cl>CS(C)=O>[N:19]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[C:6](=[O:16])[NH:5]3)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[CH:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5798BenzimidazoleHCID 14797Potassium HydroxideHCID 99912306-Fluoro-7-nitro-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 9973454HCID 9973454, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A dry DMSO solution containing 1.2 g of 6-fluoro-7-nitroquinoxaline-2,3-(1H,4H)-dione, 740 mg of potassium hydroxide powder and 1.3 g of benzimidazole was stirred with heating at 130° C. for 5.5 hours. The reaction mixture was then poured in ice-water, followed by addition of hydrochloric acid, and the mixture was filtered at pH about 9 to separate insolubles. The filtrate was then adjusted to pH about 7 with hydrochloric acid, whereupon crystals separated out again. These crystals were collected by filtration to provide 210 mg of 6-(benzimidazol-1-yl)-7-nitroquinoxaline-2,3-(1H,4H)-dione.

Workup

  1. filtrationthe mixture was filtered at pH about 9
  2. customto separate insolubles
  3. customseparated out again
  4. filtrationThese crystals were collected by filtration

Sources & evidence

ORD record
ord-5dfaf9000b9147e7952ec7b2c71d6797
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

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