2-Chloroaniline → HCID 2747545, compound

HRID 1478094Notes

Reaction equation

HRID 1478094 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-fa375dac15bc47a2814e1379fde196dc
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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