Triethylamine → N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamide

HRID 1754112Notes

Reaction equation

HRID 1754112 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na+].[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.CCN(CC)CC.[NH4+].[OH-]>O1CCOCC1.CS(C)=O.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Cu+2].CCOC(C)=O>[F:15][C:16]([F:27])([F:28])[O:17][C:18]1[CH:23]=[C:22]([S:11]([C:8]2[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=2)(=[O:13])=[O:12])[CH:21]=[CH:20][CH:19]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 23666794Sodium 4-acetamidobenzene-1-sulfinate

Product 1

HCID 70978998N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamideYield 57.9%

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of sodium 4-acetamidobenzenesulfinate dehydrate (128 mg, 0.5 mmol), 3-trifluoromethoxy-phenylboronic acid (144 mg, 0.75 mmol) and Et3N (0.313 mL, 2.25 mmol) in 1,4-dioxane (4 mL) and DMSO (4 mL) is added Cu(OAc)2 (114 mg, 0.625 mmol). The mixture is heated at 60° C. for 16 h then cooled to ambient temperature. EtOAc (12 ml) and brine (6 ml) is added followed by concentrated NH4OH (0.6 mL) and the mixture is stirred at ambient temperature for 15 min. The layers are separated and the aqueous layer is extracted with EtOAc (6 mL). The combined extracts are dried (Na2SO4) and evaporated. The residue is purified by preparative TLC with 2:1 EtOAc/hexanes to give 104 mg (57%) white solid.

Workup

  1. temperaturethen cooled to ambient temperature
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with EtOAc (6 mL)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. customevaporated
  6. customThe residue is purified by preparative TLC with 2:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-8008021cc14c4081b4213b819b0bdec4
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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