1,2-Dichloroethane → 4,5-difluoro-N-methyl-2-nitrobenzamide

HRID 1887698Notes

Reaction equation

HRID 1887698 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:28][CH3:26])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 42196304,5-Difluoro-2-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 619939344,5-difluoro-N-methyl-2-nitrobenzamideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4,5-difluoro-2-nitrobenzoic acid (1.872 g, 9.22 mmol), methylamine hydrogen chloride (0.75 g, 1.2 eq), EDC (2.12 g, 1.2 eq), HOBt (1.5 g, 1.2 eq) in DMF (20 mL) was added DIEA (5.0 mL, 3.0 eq). The mixture was stirred at room temperature for 15 min. It was concentrated and the crude was dissolved in EtOAc. It was washed with a saturated NaHCO3. The solvent was removed and the crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex) to obtain the desired product 4,5-difluoro-N-methyl-2-nitrobenzamide (1.33 g, isolated yield 67%).

Workup

  1. concentrationIt was concentrated
  2. dissolutionthe crude was dissolved in EtOAc
  3. washIt was washed with a saturated NaHCO3
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex)

Sources & evidence

ORD record
ord-fd3f9e7265604aed877b91aafb4e3ad3
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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