Benzoyl chloride, 3-(chlorosulfonyl)- → 3-{[(4-Isopropoxyphenyl)amino]carbonyl}benzenesulfonyl chloride

HRID 1967542Notes

Reaction equation

HRID 1967542 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH:14]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[CH:14]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:8]([C:7]2[CH:6]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:20][CH:19]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 821124-Isopropoxyaniline

Product 1

HCID 866497913-{[(4-Isopropoxyphenyl)amino]carbonyl}benzenesulfonyl chlorideYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(Chlorosulfonyl)benzoyl chloride (5.00 g) was added to a toluene (50 mL) solution of 4-isopropoxyaniline (3.17 g), and stirred overnight at room temperature. The solid in the reaction system was removed through filtration, and the filtrate was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient), then the resulting compound was suspended in diisopropyl ether added thereto, and the solid was collected through filtration to give the entitled compound (2.27 g, 35%) as a pale blue solid.

Workup

  1. customThe solid in the reaction system was removed through filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient)
  4. additionadded
  5. filtrationthe solid was collected through filtration

Sources & evidence

ORD record
ord-916e14810fb746b3ae7ab38b7fcaa472
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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