3-Amino-4-chlorophenol → N-(2-chloro-5-hydroxyphenyl)-2-(4-methanesulfonylbenzyl)-3-oxo-butyramide

HRID 2266500Notes

Reaction equation

HRID 2266500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(S[C:15](=[O:31])[CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:17](=[O:19])[CH3:18])(C)(C)C>COCCOC.FC(F)(F)C([O-])=O.[Ag+]>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=1[NH:1][C:15](=[O:31])[CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:23][CH:22]=1)[C:17](=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 50700783-Amino-4-chlorophenolHCID 866314382-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

Product 1

HCID 86631439N-(2-chloro-5-hydroxyphenyl)-2-(4-methanesulfonylbenzyl)-3-oxo-butyramide

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Silver trifluoroacetate (1.3 g) was added in two portions over 20 minutes to a stirred solution of 3-amino-4-chlorophenol (0.5 g) and 2-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl ester (0.8 g) in 1,2-dimethoxyethane (10 mL) at room temperature. The mixture was stirred at room temperature for 15 hours and then filtered through hyflo, washing with 1,2-dimethoxyethane. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) gave title compound as a pale peach solid, 0.75 g.

Workup

  1. filtrationfiltered through hyflo
  2. washwashing with 1,2-dimethoxyethane
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume)

Sources & evidence

ORD record
ord-8087aff0159c435f93a478a972f26a63
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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