Ethyl chloroformate → o-Ethoxycarbonylbenzamidoxime

HRID 1195796Notes

Reaction equation

HRID 1195796 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].Cl.[C:8](=[N:16][OH:17])([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[CH2:3]([O:2][C:1]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8](=[N:16][OH:17])[NH2:15])=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 53395560Benzamidoxime hydrochloride

Product 1

HCID 86745772o-Ethoxycarbonylbenzamidoxime

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Following the known process [Ber, 18, 2467 (1875)], a solution of 13.4 ml (0.14 mol) of ethyl chlorocarbonate in 100 ml of chloroform was added dropwise to a solution of 38.2 g (0.28 mol) of benzamidoxime hydrochloride in 380 ml of chloroform. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 3 hours. The benzamidoxime thus precipitated was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in 100 ml of ethyl alcohol, to which 30 ml, of water were added. Most ethyl alcohol was then distilled off under reduced pressure. Crystals thus formed were collected by filtration, washed with water and then dried under reduced pressure, whereby the title compound was obtained as colorless crystals.

Workup

  1. additionAfter completion of the dropwise addition
  2. customThe benzamidoxime thus precipitated
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml of ethyl alcohol, to which 30 ml, of water
  6. additionwere added
  7. distillationMost ethyl alcohol was then distilled off under reduced pressure
  8. customCrystals thus formed
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. dry with materialdried under reduced pressure, whereby the title compound
  12. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-3da0b65f184c44a0b41acf88ef98320d
Source dataset
uspto-grants-1992_05
Patent number
US05112841

Reaction notes

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