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

HRID 2226858Notes

Reaction equation

HRID 2226858 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8cb83c062e884f5db4b827903d07f291
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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