Sodium Thiosulfate → HCID 22132747, compound

HRID 1857259Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[N+:33]([O-])=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl.CO.O>[NH2:33][C:3]1[CH:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[O:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(4-Chloro-3-nitrophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea (100 mg) was dissolved in chloroform/methanol/water (5ml/15ml/3ml), sodium thiosulfate (358 mg) was added, and the admixture was stirred at 60° C. for 20 minutes. The reaction mixture was extracted 2 times with chloroform, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 39 mg of the title compound (yield: 41%).

Workup

extractionThe reaction mixture was extracted 2 times with chloroform
washthe organic layer was then washed with brine
dry with materialdried with anhydrous sodium sulfate
customThe solvent was removed by reduced-pressure distillation
customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record: ord-6cf80344b2f54b73b846901ea5af1b5d
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143764

Reaction notes

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