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Tetrahydrofuran → 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 453586
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HRID 453586 반응식
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([O:12]CC)=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17].O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([OH:12])=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17]
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5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59411376ethyl 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylate

생성물 1

HCID 594113852-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid수율 91%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

To a mixture of ethyl 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylate (8.39 g), tetrahydrofuran (50 mL) and ethanol (50 mL) was added 8N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated, 6N hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. Crystallization from diethyl ether gave 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (7.07 g, yield 91%) as brown crystals.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. addition6N hydrochloric acid was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customCrystallization from diethyl ether

출처 및 근거

ORD 기록
ord-e882d971e98d48fca68378e25c0152a7
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492405B2

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