Benzenesulfonyl chloride → N-(3,5-dichlorophenyl)benzenesulfonamide

HRID 2284381Notes

Reaction equation

HRID 2284381 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[NH2:24]>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 122813,5-DichloroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 4985978N-(3,5-dichlorophenyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (1.74 mL, 13.57 mmol) and DIEA (0.34 mL, 2.49 mmol) were added to a solution of 3,5-dichloroaniline (2.0 g, 12.34 mmol) in DCM (50 mL). The resulting solution was stirred at room temperature for 48 h, during which a precipitate was formed. The reaction mixture was then evaporated to dryness and purified by flash column chromatography (ethyl acetate/hexanes=1/9) to give TC-IV-145 (1.90 g, 51%) as a yellow solid.

Workup

  1. customwas formed
  2. customThe reaction mixture was then evaporated to dryness
  3. custompurified by flash column chromatography (ethyl acetate/hexanes=1/9)
  4. customto give TC-IV-145 (1.90 g, 51%) as a yellow solid

Sources & evidence

ORD record
ord-50784e1822e1405ca65999300c9a57bd
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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