2-Aminobenzenesulfonamide → HCID 42643894, compound

HRID 2283279Notes

Reaction equation

HRID 2283279 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]([C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[S:24](Cl)(=[O:26])=[O:25])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1.CO.CCOC(C)=O>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][S:24]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:26])=[O:25])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 43142223HCID 43142223, compound

Product 1

HCID 42643894HCID 42643894, compoundYield 47.1%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

2-Aminobenzenesulfonamide (0.057 g, 0.33 mmol) was dissolved in pyridine (2.5 mL) followed by addition of (E)-2-(4-tert-butylphenyl)ethenesulfonyl chloride (0.078 g, 0.30 mmol) and the reaction was stirred at RT overnight. The solvent was then removed under reduced pressure and the pale yellow oily residue was used in the next step without further purification. The crude material (0.118 g, 0.3 mmol) was dissolved in MeOH (5 mL) with a few drops of EtOAc and was subjected to reduction using the H-cube instrument. The reaction mixture was eluted through the Pd/C (10%) cartridge using full hydrogen (1 atm) at 1 ml/min. The mixture was subjected to the H-cube once again using the same conditions for full conversion of the starting material and purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (56 mg, 47%) as a white solid.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe pale yellow oily residue was used in the next step without further purification
  3. washThe reaction mixture was eluted through the Pd/C (10%) cartridge
  4. custompurified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record
ord-e2e40618419e44cfb30b54c74c1f4e87
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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