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Methanol → 3-(5,6,7,8-Tetrahydronaphthalene-2-sulfonamido)thiophene-2-carboxylic acid

HRID 1925720
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HRID 1925720 반응식
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12].[OH-].[Na+].CO>O1CCCC1>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([OH:22])=[O:21])(=[O:12])=[O:13]
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참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 8823208Methyl 3-(5,6,7,8-tetrahydronaphthalene-2-sulfonamido)thiophene-2-carboxylate

생성물 1

HCID 251838033-(5,6,7,8-Tetrahydronaphthalene-2-sulfonamido)thiophene-2-carboxylic acid수율 75.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of 78 (71 mg, 0.20 mmol) in tetrahydrofuran (1 mL) were added aqueous sodium hydroxide (2 mL; 2N) and methanol (2 mL). The reaction mixture was heated at 50° C. for 27 hours, allowed to cool to room temperature, and then extracted with aqueous sodium hydroxide (20 mL; 2N). The aqueous layer was washed with diethyl ether (30 mL×2), acidified with aqueous hydrochloric acid (20 mL; 6N), and extracted with dichloromethane (40 mL). The organic layer was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to yield the title compound as a white solid (51 mg).

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with aqueous sodium hydroxide (20 mL; 2N)
  3. washThe aqueous layer was washed with diethyl ether (30 mL×2)
  4. extractionextracted with dichloromethane (40 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-37fd85cd399e48c38f2dde5db8706cb9
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178699B2

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