Acetic Acid → HCID 563387, compound

HRID 68538Notes

Reaction equation

HRID 68538 reaction equation
C([O:3][C:4]([NH:6][C:7](=[O:19])[C:8]([C:17]#[N:18])=[N:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)C.C([O-])(=O)C.[Na+].C(O)(=O)C>O>[C:11]1([N:10]2[C:4](=[O:3])[NH:6][C:7](=[O:19])[C:8]([C:17]#[N:18])=[N:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 2822520Ethyl[2-cyano-2-(2-phenylhydrazono)acetamido]formate

Product 1

HCID 563387HCID 563387, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate b (21 g, 0.08 mol) and anhydrous sodium acetate (29 g, 0.35 mol) were added to glacial acetic acid (20v/w, 420 mL). The mixture was warmed up to react under reflux for 2 h. After completion of the reaction, the reaction solution was cooled to 0° C. and poured into water (1200 mL). The mixture was stirred for 30 min and filtered by suction. The filtered cake was washed with water and petroleum ether, and dried to produce an orange red solid (12 g) in a yield of 67.8%.

Workup

  1. temperatureThe mixture was warmed up
  2. customto react
  3. temperatureunder reflux for 2 h
  4. customAfter completion of the reaction
  5. filtrationfiltered by suction
  6. washThe filtered cake was washed with water and petroleum ether
  7. customdried

Sources & evidence

ORD record
ord-105a12909b6245179ca0ecfa4091af6a
Source dataset
uspto-grants-2014_09
Patent number
US08822465B2

Reaction notes

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