Citric Acid → N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

HRID 2079603Notes

Reaction equation

HRID 2079603 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 57788151N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chloroaniline (400 mg, 3.13 mmol) in anhydrous dichloromethane (40 mL) were added 3-methoxybenzenesulfonyl chloride (648 mg, 3.13 mmol) followed by pyridine (297.2 mg, 3.76 mmol). The mixture was allowed to stir for 12 h at 25° C. 10% citric acid solution (20 mL) and water (20 mL) was added. The organic phase was dried (Na2SO4), and evaporated under reduced pressure yielding the title compound as solid which was used as such in the next step. Yield: 900 mg (96%). MS (m/e): 296 (M+−H); 1H-NMR (CDCl3, 400 MHz): δ 3.76 (s, 3H), 6.48 (brs, 1H), 7.0 (d, J=8.72 Hz, 2H), 7.06 (d, J=7.76 Hz, 1H), 7.21 (m, 3H), 7.32 (m, 2H).

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bf36f5f2bdfa42f99f69fd1332a065ac
Source dataset
uspto-grants-2011_04
Patent number
US07932269B2

Reaction notes

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