Potassium Carbonate → HCID 21489133, compound

HRID 1974250Notes

Reaction equation

HRID 1974250 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C(#N)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][Cl:20])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 141831Benzeneethanol, 4-amino-, acetate (ester)

Product 1

HCID 21489133HCID 21489133, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

17.9 gm (0.1 mol) of p-aminophenethyl acetate were dissolved in 180 ml of acetonitrile, 27.6 gm (0.2 mol) of potassium carbonate were added to the solution, and then, while stirring, 17.0 gm (0.12 mol) of 4-chlorobutyric acid chloride were added dropwise. The resulting mixture was stirred for 2 hours at room temperature, thereafter heated to 50° C and then vacuum-filtered to remove precipitated inorganic salts. The solvent was distilled out of the filtrate in vacuo, and the residue was recrystallized from isopropanol, yielding 14.8 gm (52.2% of theory) of p-(4-chlorobutyramido)-phenethyl acetate, m.p. 83° C.

Workup

  1. stirringThe resulting mixture was stirred for 2 hours at room temperature
  2. filtrationvacuum-filtered
  3. customto remove
  4. customprecipitated inorganic salts
  5. distillationThe solvent was distilled out of the filtrate in vacuo
  6. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-4abc347bf7644f229378ad0d68e7e787
Source dataset
uspto-grants-1976_12
Patent number
US04000274

Reaction notes

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