Reaction equation
C(CS[C:6](=[S:12])[S:7][CH2:8][C:9]([OH:11])=O)(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:25]1[C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=[C:27]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:26]=1.Cl.C(N(CC)C(C)C)(C)C.Cl>O1CCCC1>[S:33]([C:27]1[CH:26]=[CH:25][C:30]([CH2:31][N:32]2[C:9](=[O:11])[CH2:8][S:7][C:6]2=[S:12])=[CH:29][CH:28]=1)(=[O:34])(=[O:35])[NH2:36]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of bis(carboxymethyl)trithiocarbonate (200 mg) in tetrahydrofuran (10 ml) was added carbonyldiimidazole (291 mg), and the mixture was stirred at room temperature. After 2 hr, to the reaction mixture were added homosulfamine hydrochloride (200 mg) and N,N-diisopropylethylamine (155 mg), and the mixture was stirred overnight at 70° C. 2N Hydrochloric acid (10 ml) was added thereto under ice cooling, the mixture was extracted twice with ethyl acetate (40 ml), and the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2:1) to give 3-(4-sulfamoylbenzyl)-2-thioxothiazolidin-4-one (189 mg).
Workup
- stirringthe mixture was stirred overnight at 70° C
- extractionunder ice cooling, the mixture was extracted twice with ethyl acetate (40 ml)
- dry with materialthe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-67e3bd37cd1e4a92ac033706125b7538
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056862B2
Linked notes
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