Triethylamine → 2-amino-4-chloro-N-methoxy-N-methylBenzamide

HRID 275862Notes

Reaction equation

HRID 275862 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[CH3:13][N:14]([O:15][CH3:16])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[NH2:1]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 666462-Amino-4-chlorobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 222292422-amino-4-chloro-N-methoxy-N-methylBenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-chlorobenzoic acid (3 g) and N,O-dimethylhydroxylamine hydrochloride (1.9 g) were dissolved in a mixture of methylene chloride (40 ml) and N,N-dimethylformamide (4 ml). To the solution were added, while stirring at room temperature, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide-hydrochloride (3.6 g) and triethylamine (1.4 g). The mixture was stirred for 90 minutes, which was then concentrated under reduced pressure. To the concentrate were added ethyl acetate (100 ml) and-water (100 ml). The mixture was shaken, The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off, and the residue was purified by means of a silica gel chromatography to give N-methyl-N-methyloxy-2-amino-4-chlorobenzamide as a yellow oily product (3.0 g).

Workup

  1. additionTo the solution were added
  2. stirringThe mixture was stirred for 90 minutes
  3. concentrationwhich was then concentrated under reduced pressure
  4. additionTo the concentrate were added ethyl acetate (100 ml)
  5. stirringThe mixture was shaken
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off
  9. customthe residue was purified by means of a silica gel chromatography

Sources & evidence

ORD record
ord-3d1158e6b39041f890989d5deced15f1
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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