Dimethylformamide → HCID 57458240, compound

HRID 238352Notes

Reaction equation

HRID 238352 reaction equation
CN(C)C=O.Br[C:7]1[CH:8]=[C:9]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].C(N(CC)CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:17][Si:18]([C:21]#[C:22][C:7]1[CH:8]=[C:9]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1)([CH3:20])[CH3:19]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 27347653-Bromobenzene-1-sulfonamide

Product 1

HCID 57458240HCID 57458240, compoundYield 85.3%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A dimethylformamide (30 mL) solution of 3-bromobenzenesulfonamide (13.7 g), trimethylsilylacetylene (5.18 g), copper(I) iodide (65 mg), bis(triphenylphosphine)palladium(II) dichloride (400 mg), triphenylphosphine (300 mg) and triethylamine (15.0 mL) was stirred at 80° C. for 6 hours. Thereafter, the reaction solution was added to water, and the obtained solution was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel 60 N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (11.4 g) in the form of a light brown solid.

Workup

  1. extractionthe obtained solution was then extracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel 60 N, hexane:ethyl acetate=4:1 to 3:1)

Sources & evidence

ORD record
ord-637e17ccc9364bf2855e2fd9fbcee922
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

Loading…