Methanol → 2-(Benzamido)-4-((phenylthio)methyl)benzoic acid

HRID 1673409Notes

Reaction equation

HRID 1673409 reaction equation
[OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([CH2:24][S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:5]([NH:13][C:14]1[CH:23]=[C:22]([CH2:24][S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16]([OH:18])=[O:17])(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 57879308HCID 57879308, compound

Product 1

HCID 578795772-(Benzamido)-4-((phenylthio)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.50 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 3 mL of methanol and 3 mL of tetrahydrofuran containing 0.29 g of methyl 2-(benzamido)-4-((phenylthio)methyl)benzoate while ice-cooled and stirred at room temperature for 5 hours. 0.25 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise and stirred at the same temperature for 14 hours. The solvent was evaporated under reduced pressure and water was added and pH was adjusted to pH 4.0 with 1.0 mol/L hydrochloric acid. A solid substance was separated by filtration to obtain 0.28 g of 2-(benzamido)-4-((phenylthio)methyl)benzoic acid as white solid.

Workup

  1. temperaturecooled
  2. stirringstirred at the same temperature for 14 hours
  3. customThe solvent was evaporated under reduced pressure and water
  4. additionwas added
  5. customA solid substance was separated by filtration

Sources & evidence

ORD record
ord-f7e426e2eb304470b16098830476c175
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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