Potassium Carbonate → N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)-N2-[(4-fluorophenyl)sulfonyl]glycinamide

HRID 1009482Notes

Reaction equation

HRID 1009482 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:21][C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([N:8]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:10])=[O:11])[CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 711089N-(3-chloro-2-methylphenyl)-4-fluorobenzenesulfonamideHCID 467366912-Bromo-N-(4-methoxybenzyl)acetamide

Product 1

HCID 58009677N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)-N2-[(4-fluorophenyl)sulfonyl]glycinamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

449 mg of N-(3-chloro-2-methylphenyl)-4-fluorobenzenesulfonamide was dissolved in 3.00 mL of DMF, and 387 mg of 2-bromo-N-(4-methoxybenzyl)acetamide and 207 mg of potassium carbonate were added thereto, followed by stirring at room temperature overnight. To the reaction liquid was added an aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform, and the organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain a product, which was crystallized from hexane/ethyl acetate to obtain 466 mg of N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)-N2-[(4-fluorophenyl)sulfonyl]glycinamide.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)
  7. customto obtain a product, which
  8. customwas crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-68157fb626c643b98a7a41f6861b1386
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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