3-Phenoxyphenol → N-(2-chloro-4-sulfamoyl-phenyl)-2-(3-phenoxyphenoxy)acetamide

HRID 1157391Notes

Reaction equation

HRID 1157391 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[NH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29]Br)=[C:23]([Cl:32])[CH:22]=1)(=[O:20])=[O:19]>CN(C=O)C>[NH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29][O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)=[C:23]([Cl:32])[CH:22]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 128423-PhenoxyphenolHCID 24758Sodium hydrideHCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

Product 1

HCID 12000658N-(2-chloro-4-sulfamoyl-phenyl)-2-(3-phenoxyphenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 37 mg (0.198 mmol) of 3-phenoxyphenol (1-1) in 1 mL anhydrous DMF under nitrogen was treated with 10 mg (0.397 mmol) of 60% NaH dispersion. The resulting mixture was stirred at room temperature for 4 hours and then treated with 65 mg (0.198 mmol) of N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (A-3). This mixture was then stirred at room temperature for an additional 4 hours. The reaction was concentrated in vacuo, and the residue was purified by reverse phase prep LC on a Gilson unit. Clean product fractions were combined and concentrated in vacuo to give the desired product 1-2 as a white solid. MS: M+1=433.2.

Workup

  1. stirringThis mixture was then stirred at room temperature for an additional 4 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was purified by reverse phase prep LC on a Gilson unit
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcabe0f73c3b4b99a9c254a7620d1909
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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