Propionic Acid → HCID 10330023, compound

HRID 1702180Notes

Reaction equation

HRID 1702180 reaction equation
[N:1]([O-])=O.[Na+].[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:6].[C:13]([OH:17])(=O)[CH2:14][CH3:15].C(OC(=O)CC)(=O)CC.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[C:8]([CH:7]([C:5]#[N:6])[NH:1][C:13](=[O:17])[CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 7764Ethyl cyanoacetateHCID 24489Sodium DithioniteHCID 31263Propionic anhydrideHCID 23668193Sodium Nitrite

Product 1

HCID 10330023HCID 10330023, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 16 g. sodium nitrite, 60 ml. water and 22.6 g. ethyl cyanoacetate cooled to approximately 5° C. was added 16 ml. propionic acid. After stirring the reaction mixture at 0°-5° C. for 1.5 hours, 200 g. ice and 50 ml. propionic anhydride were added. Finally, 70 g. sodium hydrosulfite was added in portions over a time period of from about 5 to about 10 minutes. Stirring was continued for one hour, and the precipitated solid was collected by filtration. The solids were then washed with 60 ml. hot acetone and recrystallized from ether-petroleum ether. The structure was verified by NMR. Yield 6.8 g.

Workup

  1. additionwas added 16 ml
  2. stirringStirring
  3. waitwas continued for one hour
  4. filtrationthe precipitated solid was collected by filtration
  5. washThe solids were then washed with 60 ml
  6. customhot acetone and recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-e68924b9f6e0427e96b5a3969bbe4029
Source dataset
uspto-grants-1983_04
Patent number
US04380641

Reaction notes

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