Acrylamide → HCID 67635981, compound

HRID 53327Notes

Reaction equation

HRID 53327 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:5]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.[C:24]([NH2:28])(=[O:27])[CH:25]=[CH2:26].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl.O>[C:24]([CH:25]=[CH:26][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:5]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[OH:9])[CH:7]=1)(=[O:27])[NH2:28]

Participants

9

Reactant 4

HCID 6579AcrylamideHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 54363139HCID 54363139, compound

Product 1

HCID 67635981HCID 67635981, compoundYield 59.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-[3-bromo-5-[(4-fluorophenyl)hydroxymethyl]phenyl]-2-propenoate (9.50 g), acrylamide (2.67 g), palladium(II) acetate (0.306 g), tri-o-tolylphosphine (0.763 g) and triethylamine (3.80 g) in acetonitrile (10 ml) was heated to 100° C. for 4 hours under an atmosphere of nitrogen and then cooled. Water (150 ml) and dichloromethane (150 ml) was added and the mixture was warmed with stirring to disperse the solid residue. The mixture was cooled and filtered, and the solid was dissolved in hot isopropanol (500 ml). The solution was filtered hot using a filter aid, and the filtrate was concentrated until crystallisation commenced. An equal volume of ether was added and the mixture was allowed to cool. The solid was filtered off and dried to give the title compound (5.50 g), m.p. 197°-199° C. Found: C,68.55; H,5.17; N,4.01. C21H20FNO4 requires C,68.28; H,5.46; N,3.79%.

Workup

  1. temperaturecooled
  2. temperaturethe mixture was warmed
  3. additionto disperse the solid residue
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. dissolutionthe solid was dissolved in hot isopropanol (500 ml)
  7. filtrationThe solution was filtered hot
  8. concentrationthe filtrate was concentrated until crystallisation
  9. additionAn equal volume of ether was added
  10. temperatureto cool
  11. filtrationThe solid was filtered off
  12. customdried

Sources & evidence

ORD record
ord-bdc0c8ecc8f345fe9cfcea771486fa4d
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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