Hydrochloric Acid → 4-((4-Oxo-2-thioxothiazolidin-3-yl)methyl)benzenesulfonamide

HRID 2172832

반응식

HRID 2172832 반응식
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]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 67313Mafenide HydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 806183,5-Dithia-4-thioxo-1,7-heptanedioic acidHCID 81531Diisopropylethylamine

생성물 1

HCID 336793594-((4-Oxo-2-thioxothiazolidin-3-yl)methyl)benzenesulfonamide수율 70.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  1. stirringthe mixture was stirred overnight at 70° C
  2. extractionunder ice cooling, the mixture was extracted twice with ethyl acetate (40 ml)
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-67e3bd37cd1e4a92ac033706125b7538
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056862B2

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