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

HRID 2226858
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인쇄 미리보기

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HRID 2226858 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8cb83c062e884f5db4b827903d07f291
출처 데이터셋
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05350748

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