Water → Methyl 4-[[4-(benzoylamino)phenyl]methoxy]benzenepropanoate

HRID 2422226Notes

Reaction equation

HRID 2422226 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>O1CCCC1>[C:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 23143251Methyl 3-(4-((4-aminobenzyl)oxy)phenyl)propanoate

Product 1

HCID 57541946Methyl 4-[[4-(benzoylamino)phenyl]methoxy]benzenepropanoateYield 134.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(4-aminophenyl) methoxy]benzenepropanoate (0.13 g, 0.44 mmol) and triethylamine (0.50 mL) in tetrahydrofuran (9 mL) was added benzoyl chloride (74 mg, 0.53 mmol), and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.23 g, quantitative). oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1)

Sources & evidence

ORD record
ord-82b5939e5f03423795816bb7a6f8e104
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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