Triethylamine → HCID 86063601, compound

HRID 729992Notes

Reaction equation

HRID 729992 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])C=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:47](CC)CC)C>C1COCC1.[Cu]I>[N+:15]([C:5]1[C:6]([NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[N:47][C:2]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:3][CH:4]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 64591585HCID 64591585, compound

Product 1

HCID 86063601HCID 86063601, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add propane-2-sulfonic acid (5-chloro-2-nitrophenyl)amide (10 g, 35.7 mmol), phenylacetylene (5.9 mL, 53.6 mmol) and triphenylphosphine (0.46 g, 1.78 mmol) to a solution of triethylamine (25 mL, 178.5 mmol) in dry THF (25 mL) and flush the system with nitrogen. Add dichlorobis(triphenylphosphine)palladium(1) (0.625 g, 0.89 mmol) and copper (I) iodide (0.17 g, 0.89 mmol) to this stirring mixture. Heat the reaction to reflux for 4 h. Cool to RT and concentrate to a slurry. Filter the crude material through a plug of silica gel using EtOAc as the eluting solvent. Concentrate the filtrate and crystallize the title compound from EtOAc-hexanes (7.9 g, 64%).

Workup

  1. customflush the system with nitrogen
  2. temperatureHeat
  3. customthe reaction
  4. temperatureto reflux for 4 h
  5. concentrationconcentrate to a slurry
  6. filtrationFilter the crude material through a plug of silica gel
  7. concentrationConcentrate the filtrate
  8. customcrystallize the title compound from EtOAc-hexanes (7.9 g, 64%)

Sources & evidence

ORD record
ord-aa9fc0bba4f74ecd9f448c178b01e416
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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