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Tetrahydrofuran → N-Methyl-N-[2-(1,3,4-thiadiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851528
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HRID 1851528 반응식
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:16][C:15](C(OCC)=O)=[N:14][N:13]=1)=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:16][CH:15]=[N:14][N:13]=1)=[CH:8]2)[S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23]
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참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136037568Ethyl 5-(7-[methyl(2-thienylsulfonyl)amino]-1h-indol-2-yl)-1,3,4-thiadiazole-2-carboxylate

생성물 1

HCID 136060818N-Methyl-N-[2-(1,3,4-thiadiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide수율 78%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

A mixture of ethyl 5-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate (0.20 g), 8N aqueous sodium hydroxide solution (0.14 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated to give the title compound (0.13 g, yield 78%) as yellow crystals. melting point 270-271° C.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried
  6. dissolutionThe obtained crystals were dissolved in tetrahydrofuran
  7. additiontreated with activated carbon
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a58cb7ea32024f4584f9445846fd77f2
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957070B2

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