p-Hydroxybenzenesulfonamide → N2-(3-chloro-2-methylphenyl)-N2-[(4-hydroxyphenyl)sulfonyl]-N-(4-methoxybenzyl)glycinamide

HRID 1009483Notes

Reaction equation

HRID 1009483 reaction equation
[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](N)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1.ClC(Cl)C>[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([N:8]([S:30]([C:27]2[CH:28]=[CH:29][C:24]([OH:23])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 74093p-HydroxybenzenesulfonamideHCID 26417493N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide

Product 1

HCID 58009381N2-(3-chloro-2-methylphenyl)-N2-[(4-hydroxyphenyl)sulfonyl]-N-(4-methoxybenzyl)glycinamideYield 22.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

200 mg of N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide was dissolved in 2.0 mL of pyridine, and a solution (2.0 mL) of 200 mg of 4-hydroxybenzenesulfonamide in dichloroethane was added thereto, followed by stirring at 80° C. overnight. The reaction liquid was concentrated under reduced pressure, to the residue was added water, followed by extraction with ethyl acetate, and the organic layer was washed with 1 M hydrochloric acid and water, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30 to 30:70), and further purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3), and the obtained residue was crystallized from diisopropyl ether to obtain 68 mg of N2-(3-chloro-2-methylphenyl)-N2-[(4-hydroxyphenyl)sulfonyl]-N-(4-methoxybenzyl)glycinamide.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, to the residue
  3. additionwas added water
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe organic layer was washed with 1 M hydrochloric acid and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30 to 30:70)
  9. customfurther purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3)
  10. customthe obtained residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-c802e5e1aaaa44e1a3b14032c0d55980
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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