Triethylamine → HCID 19047739, compound

HRID 1780809Notes

Reaction equation

HRID 1780809 reaction equation
Br[CH2:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[NH:24]C1C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[N:24]1[CH2:2][C:3]2[C:4](=[CH:9][CH:10]=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 14952469Mefenamic Acid Impurity 5（Mefenamic Acid EP Impurity E）

Product 1

HCID 19047739HCID 19047739, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6 (0.140 g), 2,3 - dimethylphenyl aniline (0.065 mL), and triethyl-amine (0.142 mL) in acetonitrile (10 mL) was refluxed 18 h. The solution was concentrated in vacuo and the residue was partitioned between methylene chloride and 2% potassium hydrogen sulfate. The methylene chloride was washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated in vacuo to afford the the product as a solid. NMR (300 MHz, CDCl3) δ 8.46 (1H, d, J=8 Hz), 8.30 (1H, d, J=8 Hz), 7.77 (1H, t, J=8 Hz), 7.24 (1H, s ), 7.22 (1H, d, J=2 Hz), 7.12 (1H, m), 5.18 (2H, s), 2.35 (3H, s), 2.14(3H, s).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between methylene chloride and 2% potassium hydrogen sulfate
  3. washThe methylene chloride was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80feea797a8a4c868b58e388456b1776
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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