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Lithium hydroxide, monohydrate → 4-[[[5-Methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoic acid

HRID 2226858
ノート
印刷プレビュー

反応式

HRID 2226858 の反応式
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9]2[S:10][C:11]([C:17]([NH:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)=[O:18])=[C:12]([S:13][CH:14]([CH3:16])[CH3:15])[C:8]=2[CH:7]=1>CO.O.C(OCC)(=O)C>[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9]2[S:10][C:11]([C:17]([NH:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)=[O:18])=[C:12]([S:13][CH:14]([CH3:16])[CH3:15])[C:8]=2[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 18963770Methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate

生成物 1

HCID 189637844-[[[5-Methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoic acid収率 78%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A suspension of lithium hydroxide-monohydrate (20 mg, 0.48 mmol) and methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate (67 mg, 0.16 mmol) in 4 mL of methanol and 2 mL of water is heated at reflux for 1.5 hours. The reaction mixture is cooled to room temperature and then diluted with ethyl acetate and washed sequentially with 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate: hexane gives 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoic acid in 78% yield; mp=241°-245° C. dec.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. washwashed sequentially with 1N HCl, water, and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationFiltration
  6. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-8cb83c062e884f5db4b827903d07f291
出典データセット
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05350748

反応ノート

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