Hydrochloric Acid → Ethyl valerimidate

HRID 1656117Notes

Reaction equation

HRID 1656117 reaction equation
Cl.[C:2](=[NH:10])([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6].C(#N)CCCC.C(O)C.Cl>C(=O)([O-])[O-].[K+].[K+]>[C:2](=[NH:10])([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8061ValeronitrileHCID 12283341Ethyl pentanimidate hydrochloride

Product 1

HCID 12283340Ethyl valerimidateYield 72%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

A 12.7 g (76.7 mmol) sample of ethyl valerimidate hydrochloride (prepared from valeronitrile, ethanol, and hydrogen chloride gas as described in A. J. Hill and I. Rabinowitz, J. Am. Chem. Soc., 1926, 48, 734) was dissolved in 33% (w/w) potassium carbonate solution (made by dissolving 15 g of K2CO3 in 30 mL of H2O) and immediately extracted with either (3×40 mL). The combined ether layers were dried over Na2SO4, filtered, and concentrated in vacuo to give 7.09 g (72%) of the product as a clear oil, which was used directly in the next step.

Workup

  1. extractionimmediately extracted with either (3×40 mL)
  2. dry with materialThe combined ether layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f3ec5b259b14689b5fd5d4a834ff014
Source dataset
uspto-grants-1993_10
Patent number
US05252574

Reaction notes

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