Sodium Carbonate → HCID 21198588, compound

HRID 1066340Notes

Reaction equation

HRID 1066340 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:14][N:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 485424Benzenemethanamine, 2,4-dichloro-N-methyl-

Product 1

HCID 21198588HCID 21198588, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10 ml N,N-dimethylformamide containing 3-fluoro-4-nitrobenzoic acid (1.00 g), N-methyl-2,4-dichlorobenzylamine (1.54 g) and sodium carbonate (1.15 g) was stirred at 100° C. for 14 hours. The reaction mixture was extracted using water and ethyl acetate with stirring. The organic layer was separated and concentrated, and then methanol was added to the resulting residue. After removal of an insoluble material, the solvent was evaporated. The resulting residue was purified by silica-gel column chromatography to give 0.85 g of 3-(N-methyl-2,4-dichlorobenzylamino)-4-nitrobenzoic acid.

Workup

  1. extractionThe reaction mixture was extracted
  2. stirringwith stirring
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. additionmethanol was added to the resulting residue
  6. customAfter removal of an insoluble material
  7. customthe solvent was evaporated
  8. customThe resulting residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-a1959f4725864a8c96c5a153843696fa
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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