Triethylamine → (E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

HRID 1272072Notes

Reaction equation

HRID 1272072 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([NH:28][S:29]([CH:32]=[CH2:33])(=[O:31])=[O:30])([CH3:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].Br[C:35]1[S:36][CH:37]=[CH:38][CH:39]=1.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:27][C:21]([NH:28][S:29](/[CH:32]=[CH:33]/[C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)(=[O:31])=[O:30])([CH3:20])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 138512-BromothiopheneHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

Product 1

HCID 86609959(E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amideYield 21.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Palladium acetate (169 mg, 0.75 mmol) and triphenylphosphine (420 mg, 1.6 mmol) were added to a solution of ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (10 g, 45.7 mmol) and 2-bromo-thiophene (3.74 mL, 39.1 mmol) in N,N-dimethylformamide (75 mL). Triethylamine (14.7 mL, 105.5 mmol) was added and the mixture was flushed with nitrogen and heated at 140° C. for 16 hours. The mixture was cooled to room temperature and 1N HCl (250 mL) was added in one portion. The mixture was extracted with ethyl acetate (3×200 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (2.5g, 21% yield).

Workup

  1. customthe mixture was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. addition1N HCl (250 mL) was added in one portion
  4. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  5. dry with materialthe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. customThe solid was purified
  10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-2a4b932c7c3f4acbb9e1f73da635052c
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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