Lithium Hydroxide → 3,5-Bis(methyl-propylcarbamoyl)-benzoic acid

HRID 1436622Notes

Reaction equation

HRID 1436622 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([C:18](=[O:24])[N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH:6]=1)C.[OH-].[Li+].C1COCC1>O>[CH3:23][N:19]([CH2:20][CH2:21][CH3:22])[C:18]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:8]=1)[C:4]([OH:25])=[O:3])=[O:24]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 688149203,5-Bis(methyl-propylcarbamoyl)-benzoic acid ethyl ester

Product 1

HCID 688146673,5-Bis(methyl-propylcarbamoyl)-benzoic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a solution of 3,5-bis(methyl-propylcarbamoyl)-benzoic acid ethyl ester (157 mg, 0.45 mmol), 1 N lithium hydroxide (2.25 mL, 2.25 mmol) and THF (2.25 mL) for 2 h at room temperature. Dilute the reaction with water (10 mL) and extract with dichloromethane (10 mL). Acidify the aqueous with 5 N HCl, extract the aqueous with dichloromethane, dry (magnesium sulfate) and concentrate to give the title compound (119 mg, 82%).

Workup

  1. additionDilute
  2. extractionextract with dichloromethane (10 mL)
  3. extractionextract the aqueous with dichloromethane
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-397e9ad831d54b298c7965d9bc33703a
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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