Triethylamine → Methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate

HRID 507006Notes

Reaction equation

HRID 507006 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[C:22](Cl)=[O:23].C(N(CC)CC)C>C1COCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[C:22]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 337778Methyl 3-amino-4-methylbenzoateHCID 27816562-Bromo-5-methoxybenzoyl chloride

Product 1

HCID 2673200Methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoateYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-amino-4-methylbenzoate (3.18 g), 2-bromo-5-methoxybenzene-1-carbonyl chloride (4.8 g) and triethylamine (5.4 ml) in THF (45 ml) were stirred at room temperature for 2.5 hour and then concentrated. The residue was dissolved in ethyl acetate and washed with 1N HCl, water, brine, dried (magnesium sulfate) and concentrated. The residue was recrystallised from hot ethyl acetate, washed with ether, and air dried to yield methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate as a white solid (5.36 g); NMR Spectrum: (DMSOd6) 2.39 (s, 3H), 3.83 (s, 3H), 3.87 (s, 3H), 7.02 (m, 1H), 7.23 (d, 1H), 7.42 (d, 1H), 7.60 (d, 1H), 7.75 (m, 1H), 8.12 (s, 1H), 10.06 (s, 1H); Mass Spectrum: M+H+ 377.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N HCl, water, brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customThe residue was recrystallised from hot ethyl acetate
  7. washwashed with ether, and air
  8. customdried

Sources & evidence

ORD record
ord-6ea55001b4594ff7bc0ae99132bbd492
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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