Water → 2-[(methylsulfonyl)(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide

HRID 1510249Notes

Reaction equation

HRID 1510249 reaction equation
[NH:1]([CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>ClCCl>[CH3:30][S:31]([N:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)=[O:10])(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 159813822-anilino-N-[4-(4-pyridinyl)phenyl]acetamide

Product 1

HCID 576639462-[(methylsulfonyl)(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide (40.0 mg) in dichloromethane (0.80 mL) were added pyridine (0.0533 mL) and methylsulfonyl chloride (0.0204 mL) at 0° C. and the mixture was stirred at ambient temperature for 2 days. Water (4.0 mL) was added to the mixture at ambient temperature and the mixture was extracted with ethyl acetate (6.0 mL). The organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (4% methanol in chloroform) to afford 2-[(methylsulfonyl)(phenyl)amino]-N-[4-(4-pyridinyl)phenyl]acetamide (31.4 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (6.0 mL)
  2. washThe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (4% methanol in chloroform)

Sources & evidence

ORD record
ord-4e14c6332efc4e81bb6edadfd7535b79
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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