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Sodium Dithionite → Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetate

HRID 1258377
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HRID 1258377 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:5](=[N:12]/[S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])/[CH:4]=[C:3]1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 24489Sodium DithioniteHCID 58398202ethyl 2-[(4E)-1-oxo-4-thiophen-2-ylsulfonyliminonaphthalen-2-yl]sulfanylacetate

생성물 1

HCID 44608823Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetate수율 58.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

52 mg (E)-ethyl 2-(1-oxo-4-(thiophen-2-ylsulfonylimino)-1,4-dihydronaphthalen-2-ylthio)acetate (8a) was dissolved in 2 ml THF, to which was added 2 ml aqueous solution containing 107 mg Na2S2O4. The resulting biphasic solution was stirred at r.t. for 1 h until it turned pale yellow. The mixture was diluted with ethyl acetate and washed with water and brine. Dried over Na2SO4, the organic solution was filtered and the filtrate was concentrated. The crude product was purified via flash column (EtOAc/Hexane) yielding 25.2 mg (58.7%) title compound, m.p.: 116-118° C.

후처리

  1. washwashed with water and brine
  2. dry with materialDried over Na2SO4
  3. filtrationthe organic solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified via flash column (EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-78c9985802c04604ac721cd6df58bf3f
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466157B2

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