Sulfuric Acid → 2-Cyano-2-(ethoxyimino)acetamide

HRID 965414Notes

Reaction equation

HRID 965414 reaction equation
S(=O)(=O)(O)O.[C:6]([CH2:8][C:9]([NH2:11])=[O:10])#[N:7].[N:12]([O-:14])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:26][CH3:27])(=O)=O>O>[C:6]([C:8](=[N:12][O:14][CH2:26][CH3:27])[C:9]([NH2:11])=[O:10])#[N:7]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6163Diethyl SulfateHCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 540712282-Cyano-2-(ethoxyimino)acetamideYield 83,740.898%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

62.5% sulfuric acid (69.5 g, 0.44 mol) was added dropwise to a suspension of 2-cyanoacetamide (84 g, 1 mol) and sodium nitrite (82.8 g, 1.2 mol) in water (130 ml), at 35° to 40° C., and the mixture was allowed to react for 3.5 hrs. Potassium carbonate (73.3 g, 0.52 mol) in water (91 ml) was added thereto and then diethyl sulfate (16.9 g, 1.1 mmol) was added dropwise at 35° to 40° C. After completion of the addition, the reaction mixture was stirred at the same temperature for 2 hrs. and cooled to 5° C. The precipitate were filtered off, washed with water and dried to give 2-cyano-2-ethoxyimino-acetamide (130 g, yield: 92.2%).

Workup

  1. customto react for 3.5 hrs
  2. additionAfter completion of the addition
  3. filtrationThe precipitate were filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8d96bee7563d4536b60182e2aae17186
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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