Acrylamide → HCID 86591781, compound

HRID 971317Notes

Reaction equation

HRID 971317 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][C:8](=[O:28])[CH2:9][N:10]([S:18]([C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[C:29]([NH2:33])(=[O:32])[CH:30]=[CH2:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:6][O:7][C:8](=[O:28])[CH2:9][N:10]([S:18]([C:21]1[CH:26]=[CH:25][C:24](/[CH:31]=[CH:30]/[C:29]([NH2:33])=[O:32])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6579AcrylamideHCID 11776TriphenylphosphineHCID 517045Sodium AcetateHCID 50889812HCID 50889812, compound

Product 1

HCID 86591781HCID 86591781, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium acetate was dissolved in water (0.5 mL). The carboxylic acid methyl ester builiding lock III, e.g. methyl{[(4-bromophenyl)sulfonyl]-4-methylanilino}acetate (398 mg, 1 mmol), in DMW (3.5 mL) was added, followed by acrylamide (78 mg, 1.11 mmol), triphenylphosphine (26.2 mg, 0.11 mmol, 10 mol %) and palladium diacetate (11.2 mg, 0.05 mmol, 5 mol %). The resulting mixture was degazed for 5 min with argon and was heated at 80° C. for 3 h. It was filtrated through celite. Water (5 mL) was added and the desired product was extracted with ethyl acetate (3×7 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent The desired product, e.g. methyl[({4-[(1E)-3-amino-3-oxo-1-propenyl]phenyl}sulfonyl)-4-methylanilino]acetate was obtained as a colorless oil, in 88% purity by HPLC (MaxPlot detection between 230 and 400 nm). This intermediate was used in the next step without further purification.

Workup

  1. filtrationIt was filtrated through celite
  2. additionWater (5 mL) was added
  3. extractionthe desired product was extracted with ethyl acetate (3×7 mL)
  4. dry with materialCombined organic phases were dried over magnesium sulfate
  5. filtrationbefore filtering
  6. customremoval of solvent The desired product

Sources & evidence

ORD record
ord-e208197cf57f4f2ea87040d8a78b41ad
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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