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

HRID 2100153Notes

Reaction equation

HRID 2100153 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:13][CH:14]=2)=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 834334HCID 834334, compound

Product 1

HCID 68654389N-[4-(4-Methoxy-benzoyl)-phenyl]-benzenesulfonamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.26 mL, 2.03 mmol) was slowly added to an ice-cooled solution of (4-amino-phenyl)-(4-methoxy-phenyl)-methanone (178) (0.42 g, 1.85 mmol) and pyridine (0.16 mL, 2.03 mmol) in dry dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 20 h then partitioned between 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 a solid. The solid was recrystallized from hot dichloromethane and methanol to give 0.451 g (66%) of the title compound 182. 1H NMR (400 MHz, DMSO-d6): δ 3.82 (s, 3 H), 7.03 (d, J=8.8 Hz, 2 H), 7.22 (d, J=8.6 Hz, 2 H), 7.57-7.65 (m, 7 H), 7.84 (d, J=7.3 Hz, 2 H), 10.87 (s, 1 H).

Workup

  1. customthen partitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. customThe solid was recrystallized from hot dichloromethane and methanol

Sources & evidence

ORD record
ord-1c8ec3e23b9f43d381a0797beb1c8c55
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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