Hydrochloric Acid → Ethyl chloro(hydroximino)acetate

HRID 1034135Notes

Reaction equation

HRID 1034135 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:8])[CH2:6]N)[CH3:3].Cl.[N:10]([O-:12])=O.[Na+]>O>[Cl:1][C:6](=[N:10][OH:12])[C:5]([O:4][CH2:2][CH3:3])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2723640Glycine ethyl ester, hydrochlorideHCID 23668193Sodium Nitrite2×

Product 1

HCID 6816376Ethyl chloro(hydroximino)acetateYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

69.8 g of glycine ethyl ester hydrochloride are initially introduced into 120 ml of water and 41 ml of concentrated hydrochloric acid. 38 g of NaNO2 in 60 ml of water are then added dropwise at -10° C. in the course of 1 hour. After half an hour, a further 42.5 ml of concentrated hydrochloric acid are added, and then, in the course of 1 hour, a further 38 g of NaNO2 in 60 ml of water. Stirring is continued for 1 hour at -10° C. The mixture is subsequently extracted with ether, and the ether phase is washed several times with water. The ether is distilled off, and the crystals are dried. In this way, 38 g (50% of theory) of ethyl 2-chloro-2-hydroximinoacetate of a melting point of 81°-82° C. are obtained.

Workup

  1. waitAfter half an hour
  2. customin the course of 1 hour
  3. extractionThe mixture is subsequently extracted with ether
  4. washthe ether phase is washed several times with water
  5. distillationThe ether is distilled off
  6. customthe crystals are dried

Sources & evidence

ORD record
ord-3fab44966e564b9690d411ecdd5a5755
Source dataset
uspto-grants-1994_05
Patent number
US05314863

Reaction notes

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