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Hydrochloric Acid → Methyl 2-(benzamido)-4-(phenethyloxy)benzoate

HRID 1673400
Notes
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Reaction equation

HRID 1673400 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([NH:24][C:25]1[CH:34]=[C:33]([OH:35])[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C(OCC)(=O)C>[C:16]([NH:24][C:25]1[CH:34]=[C:33]([O:35][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromide3×HCID 11430Potassium Carbonate2×HCID 57879368Methyl 2-(benzamido)-4-hydroxybenzoate

Product 1

HCID 57879365Methyl 2-(benzamido)-4-(phenethyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

0.13 g of potassium carbonate and 0.10 mL of (2-bromoethyl)benzene were added to 2 mL of N-dimethylformamide solution containing 0.13 g of methyl 2-(benzamido)-4-hydroxybenzoate, and stirred at room temperature for 3 hours. 0.10 mL of (2-bromoethyl)benzene was added to the reaction mixture and stirred at 50° C. for 4 hours and at 80° C. for 3 hours. After the reaction mixture was cooled to room temperature, 0.10 g of potassium carbonate and 0.10 mL of (2-bromoethyl)benzene were added and stirred at 80° C. for 2 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/b hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to obtain 0.13 g of methyl 2-(benzamido)-4-(phenethyloxy)benzoate as colorless oil.

Workup

  1. stirringstirred at 50° C. for 4 hours and at 80° C. for 3 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. stirringstirred at 80° C. for 2 hours and 30 minutes
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with a saturated sodium chloride aqueous solution
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1]

Sources & evidence

ORD record
ord-3ac770ee492a44679aadcbaa7d369e05
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07999132B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes