Sodium Thiosulfate → HCID 22032018, compound

HRID 1792445Notes

Reaction equation

[C:1]([N:20]1[CH:24]=[CH:23][C:22]([C:25]2[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=2)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:34]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[I:34][C:23]1[C:22]([C:25]2[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=2)=[N:21][N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

20 g methyl 5-(1-trityl-1H-3-pyrazolyl)-2-thiophene carboxylate and 10.6 g N-iodosuccinimide were stirred in 200 mL N,N-dimethylformamide at 80° C. for 24 hours. Additional N-iodosuccinimide, 10.6 g, was added thereto and stirred at 80° C. for 24 hours, and then an aqueous solution of sodium thiosulfate and an aqueous solution of sodium bicarbonate were added thereto and stirred for 1 hour, and the formed solid was collected by filtration. The solid was dissolved in dichloromethane and dried over magnesium sulfate, and the solvent was removed, whereby 24.5 g of the title compound was obtained as colorless crystals.

Workup

stirringstirred for 1 hour
filtrationthe formed solid was collected by filtration
dissolutionThe solid was dissolved in dichloromethane
dry with materialdried over magnesium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-4041fef8b4e54995b5089ae87eb6ab96
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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