Methanesulfonamide → 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide

HRID 2359290Notes

Reaction equation

HRID 2359290 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.C(N=C=NCCCN(C)C)C.[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:8]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 148764175-Chloro-2,4-difluorobenzoic acid

Product 1

HCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

5-chloro-2,4-difluorobenzoic acid (0.291 g, 1.511 mmol), N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.438 g, 2.285 mmol) and 4-dimethylaminopyridine (0.420 g, 3.438 mmol) were suspended in DCM (5 mL). Methanesulfonamide (0.222 g, 2.334 mmol) was added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with DCM (10 mL) and washed with aqueous HCl solution (2 M, 2×15 mL). The organic layer was dried with a phase separating cartridge and concentrated in vacuo to yield the title compound as a white solid (0.388 g):

Workup

  1. washwashed with aqueous HCl solution (2 M, 2×15 mL)
  2. customThe organic layer was dried with a phase
  3. customseparating cartridge
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b09bc9fd2054a6cb015eb3d8a29222f
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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