ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate → HCID 178515609, compound

HRID 1908247Notes

Reaction equation

HRID 1908247 reaction equation
C(O[C:4](=[O:16])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=O)C.[CH2:17]1[CH:19]([C:20]([NH2:22])=[NH:21])[CH2:18]1.Cl.CC(C)([O-])C.[K+]>CO>[CH:19]1([C:20]2[N:22]=[C:4]([OH:16])[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=3)[N:21]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 2758176ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoateHCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 178515609HCID 178515609, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution consisting of 3-(3,4-dichlorophenyl)-3-oxo-propionic acid ethyl ester (252 mg, 0.967 mmol) and MeOH were added cyclopropylcarbamidine hydrochloride (140 mg, 1.16 mmol) and potassium tert-butoxide (266 mg, 2.37 mmol). The reaction mixture was stirred at rt overnight, then concentrated. Water and CH2Cl2 were added, and the mixture was adjusted to pH 7 with glacial acetic acid. The layers were separated, and the aqueous phase was extracted with EtOAc. The organics were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound as a white solid (133 mg, 49%).

Workup

  1. concentrationconcentrated
  2. additionWater and CH2Cl2 were added
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-e12d42db77844f379676e6227e9d8550
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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