Potassium Carbonate → HCID 53982614, compound

HRID 1073239Notes

Reaction equation

HRID 1073239 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][NH2:14])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:21](Cl)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[C:24]1([CH:23]=[CH:22][C:21]([NH:14][CH2:13][CH2:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=2)=[O:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chlorideHCID 22379525HCID 22379525, compound

Product 1

HCID 53982614HCID 53982614, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-butyloxyphenyl)ethylamine (1.0 g) in acetonitrile (40 cm3) was added powdered potassium carbonate (0.80 g). Cinnamoyl chloride (1.03 g) was then added portionwise over a period of fifteen minutes and the reaction mixture was then stirred at room temperature for 6.5 hours after which distilled water (40 cm3) was added. The mixture was left to stand overnight and was then filtered and extracted several times with ethyl acetate. The combined ethyl acetate extracts were washed successively with potassium bicarbonate solution, water and 0.5M hydrochloric acid before drying over sodium sulphate and then evaporating down to give the product as a tan coloured oil (1.60 g).

Workup

  1. distillationdistilled water (40 cm3)
  2. additionwas added
  3. waitThe mixture was left
  4. waitto stand overnight
  5. filtrationwas then filtered
  6. extractionextracted several times with ethyl acetate
  7. washThe combined ethyl acetate extracts were washed successively with potassium bicarbonate solution, water and 0.5M hydrochloric acid
  8. dry with materialbefore drying over sodium sulphate
  9. customevaporating down

Sources & evidence

ORD record
ord-7c9ee856e5024ae5bd46cad6cd0e2413
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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