Sulfuric Acid → Ethyl 2-cyano-2-(hydroxyimino)acetate

HRID 965408Notes

Reaction equation

HRID 965408 reaction equation
S(=O)(=O)(O)O.[N:6]([O-:8])=O.[Na+].[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]>O>[OH:8][N:6]=[C:12]([C:10]#[N:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7764Ethyl cyanoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

62.5% sulfuric acid (603.7 g) were added dropwise to sodium nitrite (507.2 g) and ethyl cyanoacetate (791.0 g) in water (2,540 ml) at 30° to 40° C. over 2.2 hrs. under cooling. After completion of the addition, the mixture was stirred at a room temperature for 2 hrs, and the nitrogen oxide (NO2) was removed under reduced pressure, and the residue was cooled to 15° C. to separate crystals, which were filtered off and washed twice with water (150 ml) and twice with toluene (200 ml), and dried at 50° C. to give ethyl 2-hydroxyiminocyanoacetate (932.9 g, yield: 93.9%).

Workup

  1. temperatureunder cooling
  2. additionAfter completion of the addition
  3. customthe nitrogen oxide (NO2) was removed under reduced pressure
  4. temperaturethe residue was cooled to 15° C.
  5. customto separate crystals, which
  6. filtrationwere filtered off
  7. washwashed twice with water (150 ml) and twice with toluene (200 ml)
  8. customdried at 50° C.

Sources & evidence

ORD record
ord-cca05024fedd4d0b864550c8cef9d9ad
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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