Triethylamine → HCID 19047709, compound

HRID 1780814Notes

Reaction equation

HRID 1780814 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20]C1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=1[CH3:12])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 14952469Mefenamic Acid Impurity 5（Mefenamic Acid EP Impurity E）

Product 1

HCID 19047709HCID 19047709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloromethylbenzoyl chloride (2.0 g) in methylene chloride (20 mL) was added 2,3- dimethylphenylaniline (1.28 g) and triethylamine (1.47 mL). The solution was stirred 18 h, concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Upon concentration a precipitated formed which was collected and dried to obtained the product. NMR (300 MHz, DMSO-d6) δ 10.0 (1H, s), 8.02 (1H, s), 7.94 (1H, d, J=7 Hz), 7.63 (1H, d, J=7 Hz), 7.52 (1H, t, J=7 Hz). 7.10 (3H, s), 4.83 (2H, s), 2.27 (3H, s), 2.07 (3H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. concentrationUpon concentration a precipitated
  7. customformed which
  8. customwas collected
  9. customdried
  10. customto obtained the product

Sources & evidence

ORD record
ord-e76585f3b6cf4f5f93a2e5d3aed0eecc
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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