Pyridine → N-[4-(4-Methoxy-benzoyl)-phenyl]-methanesulfonamide

HRID 229252Notes

Reaction equation

HRID 229252 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:14])=[CH:9][CH:8]=1.N1C=CC=CC=1>ClCCl.CCOC(C)=O.O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=2)=[O:14])=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 834334HCID 834334, compound

Product 1

HCID 43339069N-[4-(4-Methoxy-benzoyl)-phenyl]-methanesulfonamideYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.15 mL, 1.94 mmol) was slowly added to an ice-cooled solution of (4-amino-phenyl)-(4-methoxy-phenyl)-methanone (178) (0.4 g, 1.76 mmol) and pyridine (0.16 mL, 1.94 mmol) in dry dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 20 h then diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give 0.5 g (93%) of compound 179 as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.11 (s, 3H), 3.84 (s, 3H), 7.06 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.6 Hz, 2H), 7.68-7.72 (m, 4H), 10.31 (s, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f0a7ccd73ac54ebaa8eea840292d0003
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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