Dimethylformamide → Methyl 2-(benzamido)-4-(benzyloxy)benzoate

HRID 1673398Notes

Reaction equation

HRID 1673398 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O.[C:20]([NH:28][C:29]1[CH:38]=[C:37]([OH:39])[CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:20]([NH:28][C:29]1[CH:38]=[C:37]([O:39][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57879368Methyl 2-(benzamido)-4-hydroxybenzoate

Product 1

HCID 57879324Methyl 2-(benzamido)-4-(benzyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

82 mg of potassium carbonate and 0.047 mL of benzyl bromide were added to 1 mL of N,N-dimethylformamide solution containing 80 mg of methyl 2-(benzamido)-4-hydroxybenzoate at room temperature and stirred at the same temperature for 3 hours. Ethyl acetate and 1.0 mol/L hydrochloric acrd were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain 75 mg of methyl 2-(benzamido)-4-(benzyloxy)benzoate as white solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  4. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  5. additionHexane was added to the obtained residue
  6. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-49f3e152903a4c8bbea18bccbd992250
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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