2-Chloroaniline → HCID 2747545, compound

HRID 509569Notes

Reaction equation

HRID 509569 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].CCN(CC)CC>ClCCl>[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 72402-ChloroanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 77670p-(Methylsulphonyl)benzoic acid

Product 1

HCID 2747545HCID 2747545, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(methylsulfonyl)benzoic acid 1 (1.0 g, 5 mmol) in 50 mL of dichloromethane was added thionyl chloride (5 mL). The mixture was stirred at ambient temperature for 18 hours. After removal of all solvent, the residue was dissolved in 50 mL of dichloromethane. To the solution was added o-chloroaniline (0.766 g, 6 mmol) followed by 1.4 mL of Et3N. The mixture was stirred at ambient temperature for 2 hours. After washing with 1N HCl and water, the organic layer was concentrated to give N-(2-chlorophenyl)-4-(methylsulfonyl)benzamide 3 as a solid. Yield: 1.18 g, 76%.

Workup

  1. customAfter removal of all solvent
  2. dissolutionthe residue was dissolved in 50 mL of dichloromethane
  3. stirringThe mixture was stirred at ambient temperature for 2 hours
  4. washAfter washing with 1N HCl and water
  5. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-378574fa41f34089a9669b1a8fef7a37
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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