Cesium carbonate → 3-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

HRID 2251734Notes

Reaction equation

HRID 2251734 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][C:18]=1[CH2:30][CH2:31][CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][CH2:13][O:1][C:2]2[CH:3]=[C:4]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[C:18]([CH2:30][CH2:31][CH3:32])[CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6375573-HydroxybenzenesulfonamideHCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

Product 1

HCID 586471293-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxybenzenesulfonamide (0.5 g, 2.89 mmol) and 1-(3-bromopropoxy)-4-phenoxy-2-propylbenzene (1.01 g, 2.89 mmol) with cesium carbonate (1.04 g, 3.18 mmol) in dry DMF (10 mL) was stirred at 50° C. for 5 h. The reaction suspension was cooled to room temperature and concentrated under vacuum to an orange residue. The residue was partitioned between ethyl acetate and water. The ethyl acetate phase was dried over sodium sulfate, filtered, and concentrated to an oil. The oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1) to provide the title compound.

Workup

  1. concentrationconcentrated under vacuum to an orange residue
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-069dc8b73caf44fab2da1d4dfbf381bf
Source dataset
uspto-grants-2008_01
Patent number
US07319170B2

Reaction notes

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