Triethylamine → HCID 17748075, compound

HRID 1272354Notes

Reaction equation

HRID 1272354 reaction equation
[CH3:1][C:2]([NH:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OC)=[C:18](I)[CH:17]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:2]([NH:9][S:10](/[CH:13]=[CH:14]/[C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)(=[O:12])=[O:11])([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 28009784-Chloro-2-iodoanisoleHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

Product 1

HCID 17748075HCID 17748075, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

Ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (8.5 g, 38.8 mmol) and 4-chloroiodoanisole (7.87 g, 33.0 mmol) was dissolved in N,N-dimethylformamide (65 ml). Palladium acetate (139 mg, 0.62 mmol) and triphenylphosphine (357 mg, 1.36 mmol) was added to the reaction followed by triethylamine (12.5 ml, 89.3 mmol). The reaction was flushed with nitrogen and heated at 140° C. for 16 hours. The reaction was cooled to room temperature and quenched with 1N HCl (250 ml). The aqueous solution was extracted with ethyl acetate (3×200 ml). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was dissolved in dichloromethane and purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.0 g, 46% yield).

Workup

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 1N HCl (250 ml)
  4. extractionThe aqueous solution was extracted with ethyl acetate (3×200 ml)
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. custompurified
  10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-d44128a8f7034191b481ad78c66e2f04
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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