Hydrochloric Acid → 2-(4-(3,5-Dichlorobenzamido) phenoxy)2-methylpropionic acid

HRID 1649933Notes

Reaction equation

HRID 1649933 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:20](Cl)=[O:21]>[OH-].[Na+]>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:13][CH:14]=1)=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 761913,5-Dichlorobenzoyl chlorideHCID 27749582-(4-Aminophenoxy)-2-methylpropanoic acid

Product 1

HCID 145450912-(4-(3,5-Dichlorobenzamido) phenoxy)2-methylpropionic acidYield 76%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 0.5 g 2-(4-aminophenoxy)-2-methylpropionic acid in 5 ml 2N NaOH, 0.70 ml 3,5-dichlorobenzoyl chloride was dropwise added with stirring 5 ml additional 2N NaOH was gradually added to keep the PH strongly alkaline during the reaction. After 1 hour stirring, the reaction product was acidified with HCl. The white precipitate was recrystallized from aqueous isopropanol to give 1.4 g (76%) of fine crystals MP 206-207°.

Workup

  1. additionwas gradually added
  2. customstrongly alkaline during the reaction
  3. customThe white precipitate was recrystallized from aqueous isopropanol

Sources & evidence

ORD record
ord-33df9bc89dd14c5baad0503762d4cca9
Source dataset
uspto-grants-1990_05
Patent number
US04921997

Reaction notes

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