Methanesulfonic Acid → 2-(5-(2-(Diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid

HRID 454665Notes

Reaction equation

HRID 454665 reaction equation
[OH-].[Na+].[CH2:3]([N:5]([CH2:35][CH3:36])[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:34])=[C:13]([CH:33]=1)[C:14]([NH:16][C:17]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])=[O:15])[CH3:4].CS(O)(=O)=O>O1CCOCC1>[CH2:35]([N:5]([CH2:3][CH3:4])[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:34])=[C:13]([CH:33]=1)[C:14]([NH:16][C:17]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:18]=1[C:19]([OH:21])=[O:20])=[O:15])[CH3:36]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 58508834Methyl 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate

Product 1

HCID 585088152-(5-(2-(Diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dioxane (3.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.19 mL) were added to the obtained methyl 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate (0.087 g), followed by stirring at room temperature for 2 hours and 30 minutes and then at 50 to 55° C. for 2 hours. The reaction mixture was cooled to room temperature and adjusted to a pH of 6.9 with methanesulfonic acid, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.079 g of 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid.

Workup

  1. waitat 50 to 55° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-58d888149efc438b99ef1f13e9d3d2e9
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…