Triethylamine → (E)-2-(2-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

HRID 1272360Notes

Reaction equation

HRID 1272360 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[C:21](I)=[CH:20][CH:19]=[CH:18][C:17]=1OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:2]([NH:9][S:10](/[CH:13]=[CH:14]/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[Cl:15])(=[O:12])=[O:11])([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 167414892-Chloro-1-iodo-3-methoxybenzeneHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

Product 1

HCID 86609400(E)-2-(2-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amideYield 32%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

Ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (10 g, 46 mmol) and 2-chloroiodoanisole (4.8 mL, 39.1 mmol) was dissolved in N,N-dimethylformamide (DMF) (75 mL). Palladium acetate (169 mg, 0.75 mmol) and triphenylphosphine (420 mg, 1.6 mmol) was added to the reaction mixture followed by triethylamine (14.7 mL, 106 mmol). The reaction was flushed with nitrogen and heated at 140° C. for 16 hours. The reaction was cooled to room temperature whereupon 1N HCl (275 mL) was added. The aqueous solution was extracted with ethyl acetate (3×225 mL) and the combined 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-(2-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (4.1 g, 32% yield).

Workup

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction was cooled to room temperature whereupon 1N HCl (275 mL)
  3. additionwas added
  4. extractionThe aqueous solution was extracted with ethyl acetate (3×225 mL)
  5. dry with materialthe combined 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-93bfc9824ef9424ca8c2bc41119b557c
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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