Hydrochloric Acid → HCID 57667917, compound

HRID 2191676Notes

Reaction equation

HRID 2191676 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:5])[CH3:4].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[CH2:23]([N:6]([C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])[C:3](=[O:5])[CH3:4])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 57667800HCID 57667800, compound

Product 1

HCID 57667917HCID 57667917, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% Sodium hydride 30 mg was added to N,N-dimethylformamide 2.0 mL solution of 2-(acetamido)-4-phenoxybenzoic acid 0.10 g at room temperature, and it was stirred at same temperature for 30 minutes. Benzyl bromide 0.092 mL was added to the reaction mixture at room temperature, and it was stirred at same temperature for 2 hours and 30 minutes. 60% Sodium hydride 15 mg was added to the reaction mixture at room temperature, and it was stirred at same temperature for 30 minutes. Benzyl bromide 0.022 mL was added to the reaction mixture at room temperature, and it was stirred at same temperature for 1 hour and 30 minutes. 1.0 mol/L Hydrochloric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate:acetic acid=40:10:1] to give 2-(N-benzylacetamido)-4-phenoxybenzoic acid 0.10 g of colorless oil.

Workup

  1. stirringit was stirred at same temperature for 2 hours and 30 minutes
  2. stirringit was stirred at same temperature for 30 minutes
  3. stirringit was stirred at same temperature for 1 hour and 30 minutes
  4. customThe organic layer was separated
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5330d651be6a46e8ae42bb224baddb37
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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