Triethylamine → N-(3-ethynylphenyl)-2-methylbenzamide

HRID 607386Notes

Reaction equation

HRID 607386 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11]([C:13]1[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1)#[CH:12].CCN(CC)CC>C1COCC1>[C:11]([C:13]1[CH:14]=[C:15]([NH:19][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[CH3:1])[CH:16]=[CH:17][CH:18]=1)#[CH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 24676237N-(3-ethynylphenyl)-2-methylbenzamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with 2-methylbenzoyl chloride (0.155 g, 1.00 mmol) was cooled to room temperature, and THF (10 mL) was added. 3-Ethynyl-phenylamine (0.117 g, 1.00 mmol) was added to the THF solution of the acid chloride followed by NEt3 (0.272 mL, 2.00 mmol), and the mixture was allowed to stir at 55° C. The reaction mixture was then allowed to cool to room temperature and partitioned between EtOAc (10 mL) and H2O (15 mL). The organic layer was washed with then washed once with 1M HCl (20 mL) followed by of saturated aqueous NaHCO3 (˜20 mL) and of brine (˜20 mL). The organic extracts were concentrated and the crude residue was purified by chromatography (silica gel, gradient elution EtOAc/hexanes 10 to 70%). The product containing fractions were concentrated to give the title compound as a tan solid (434 mg, 0.88 mmol, 88%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (10 mL) and H2O (15 mL)
  3. washThe organic layer was washed
  4. washwith then washed once with 1M HCl (20 mL)
  5. concentrationThe organic extracts were concentrated
  6. customthe crude residue was purified by chromatography (silica gel, gradient elution EtOAc/hexanes 10 to 70%)
  7. additionThe product containing fractions
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-8ec10cf108f6435da179d011a97b17dd
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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