Ammonia → 2-Chloro-3,4-difluorobenzamide

HRID 2046633Notes

Reaction equation

HRID 2046633 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C[N:15](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N>O.CN(C)C=O>[Cl:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100128172-Chloro-3,4-difluorobenzoic acid

Product 1

HCID 593705452-Chloro-3,4-difluorobenzamideYield 52.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-chloro-3,4-difluorobenzoic acid (2.50 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.99 g), 1-hydroxybenztriazole (2.39 g) and N,N-dimethylformamide (72 mL) was added 28% aqueous ammonia (1.6 mL) at room temperature, and the mixture was stirred for 40 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane). The obtained solid was washed with dichloromethane to give the title compound as a solid (yield: 1.30 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane)
  6. washThe obtained solid was washed with dichloromethane

Sources & evidence

ORD record
ord-8ffbb1eef77d40b9af97cc485c1d5fcf
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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