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

HRID 453586
ノート
印刷プレビュー

反応式

HRID 453586 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e882d971e98d48fca68378e25c0152a7
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492405B2

反応ノート

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