3-Aminobenzenesulfonic acid → 3-(4-Tert-butylbenzamido)benzenesulfonic acid

HRID 79097

Reaction equation

HRID 79097 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([NH:1][C:2]2[CH:3]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[O:21])=[CH:23][CH:24]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 84743-Aminobenzenesulfonic acidHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 589881093-(4-Tert-butylbenzamido)benzenesulfonic acidYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino benzenesulfonic acid (1.7 g, 10 mmol) in pyridine (100 mL) was added 4-tert-butyl benzoyl chloride (2.0 mL, 10 mmol). The reaction was stirred at room temperature 16 h and the solvent was evaporated under vacuum. The residue was dissolved in EtOAc and washed with 1 M aqueous hydrochloric acid. The aqueous washes were extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2) to obtain 3-(4-tert-butylbenzamido)benzenesulfonic acid (2.1 g, 63% yield). LC/MS: m/z 334.3 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe solvent was evaporated under vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1 M aqueous hydrochloric acid
  4. extractionThe aqueous washes were extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-9d0f7ca0e0404b92bc69741d34050640
Source dataset
uspto-grants-2014_09
Patent number
US08841483B2

Linked notes

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