2-Propenoic acid, 3-phenyl- → HCID 131722398, compound

HRID 636069Notes

Reaction equation

HRID 636069 reaction equation
COC1C=C(C=C(OC)C=1)[NH2:6].[C:12](=[O:15])([O-])[O-].[K+].[K+].[C:18](Cl)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C=C[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.S(Cl)(Cl)=O.C[C:45](C)=[O:46].O>C1C=CC=CC=1.O.C(OCC)(=O)C.CCCCCC>[CH3:45][O:46][C:32]1[CH:37]=[C:36](/[C:19](=[CH:20]\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[C:18]([NH2:6])=[O:27])[CH:35]=[C:34]([O:15][CH3:12])[CH:33]=1

Participants

11

Reactant 6

HCID 87842-Propenoic acid, 3-phenyl-HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 660233-Phenylprop-2-enoyl chlorideHCID 663013,5-DimethoxyanilineHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 131722398HCID 131722398, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 3,5-dimethoxy aniline 1 (10.3 g, 67.5 mmol) and potassium carbonate (13.9 g, 101.2 mmol) was taken in acetone-water (150 mL, 1:2) and cooled to 5° C. Cinnamoyl chloride (12.2 g, 67.5 mmol) (prepared by treatment of a solution of cinnamic acid (10 g, 67.5 mmol) in benzene (40 mL) with thionyl chloride (8 g, 67.5 mmol) at reflux temperature for 1 h.) was added in 15 min. to reaction mixture while maintaining temperature below 5° C. Reaction mixture was stirred below 5° C. for 30 min. and allowed to raise to room temperature over a period of 30 min. (TLC, hexane:ethyl acetate, 7:3, Rf=0.4). The reaction mixture was diluted with water (100 mL) and solid separated was filtered. The solid was washed with water (2×50 ml) dried under vacuum to afford 1N-(3,5-dimethoxyphenyl)-3-phenyl-(E)-2-propenamide (2) (18.1 g) in 95% yield as a off white solid. M.P. 142-145° C.

Workup

  1. temperatureat reflux temperature for 1 h.)
  2. additionwas added in 15 min. to reaction mixture
  3. temperaturewhile maintaining temperature below 5° C
  4. customReaction mixture
  5. customseparated
  6. filtrationwas filtered
  7. washThe solid was washed with water (2×50 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c290d3ddbd27448bae6b49405915c3ba
Source dataset
uspto-grants-2001_02
Patent number
US06191279B1

Reaction notes

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