Benzenesulfonamide, 3-amino- → 2-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamide

HRID 79093

Reaction equation

HRID 79093 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:26][C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>C(Cl)Cl.N1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[CH:13]=[CH:12][C:8]=2[C:9]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([NH2:36])(=[O:34])=[O:35])[CH:28]=2)=[O:11])=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 24386Thionyl ChlorideHCID 589880892-(4-Fluorophenoxy)-4-tert-butylbenzoic acid

Product 1

HCID 248552112-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamideYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-fluorophenoxy)-4-tert-butylbenzoic acid (0.11 g, 0.39 mmol) and thionyl chloride (0.28 mL, 3.9 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 4 h. The solvent was evaporated under reduced pressure, and to the resulting oil was added a solution of 3-amino-benzenesulfonamide (73 mg, 0.42 mmol) in pyridine (4 mL). The solution was stirred at room temperature 15 h. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes) to obtain a white solid which was recrystallized from EtOAc and hexanes. 2-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamide (85 mg, 50% yield) was obtained as a white solid. LC/MS: m/z 443.3 (M+H)+ at 3.49 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes)
  7. customto obtain a white solid which
  8. customwas recrystallized from EtOAc and hexanes

Sources & evidence

ORD record
ord-9f3311df790543d0b65bf661b6c85066
Source dataset
uspto-grants-2014_09
Patent number
US08841483B2

Linked notes

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