Aniline → Methyl 4-anilinocarbonylbenzoate

HRID 1242898Notes

Reaction equation

HRID 1242898 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>O.C1COCC1>[NH:14]([C:9]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=1)=[O:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 15513Monomethyl terephthalateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 4682178Methyl 4-anilinocarbonylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxycarbonyl benzoic acid (540 mg), aniline (0.27 ml), WSC (863 mg) and triethylamine (0.84 ml) were added to THF (20 ml). After the reaction mixture was stirred at room temperature for 20 hours, the reaction mixture was placed in water, and extraction was conducted using ethyl acetate-THF (1:1). The organic layer was washed with water, saturated sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried, and then concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to give the titled compound (659 mg).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d1a0abec4e264bab8b0f7c649a0a21f8
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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