P-Toluenesulfonamide → N-(p-Tolyl)-p-toluenesulphonamide

HRID 1883415Notes

Reaction equation

HRID 1883415 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CN[C@@H]1CCCC[C@H]1NC.[NH4+].[Cl-]>[Cu]I.CN(C)C=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:19][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:17])=[O:18])=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 25517Ammonium ChlorideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 69034N-(p-Tolyl)-p-toluenesulphonamideYield 96%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A 15 mL resealable Schlenk tube was charged with CuI (9.5 mg, 0.0499 mmol, 5.0 mol %), 4-iodotoluene (218 mg, 1.00 mmol), p-toluenesulfonamide (205 mg, 1.20 mmol), K2CO3 (280 mg, 2.03 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.102 mmol, 10 mol %) and N,N-dimethylformamide (1 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 100° C. for 19 h. The resulting pale brown suspension was allowed to reach room temperature, poured into 20 mL of a diluted aq NH4Cl solution, and extracted with 3×15 mL of dichloromethane. The colorless organic phase was dried (NaSO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate 2:1, 15 mL fractions). Fractions 9-16 provided 251 mg (96% yield) of the desired product as white crystals.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. extractionextracted with 3×15 mL of dichloromethane
  5. dry with materialThe colorless organic phase was dried (NaSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate 2:1, 15 mL fractions)

Sources & evidence

ORD record
ord-e100bbf1bc5e49c2a1a81ff77b2fc56e
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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