Acetic Acid → HCID 86648061, compound

HRID 2098971Notes

Reaction equation

HRID 2098971 reaction equation
[F:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=O)[CH2:8][CH2:7]2.[C:14](#[N:18])[CH2:15][C:16]#[N:17].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[C:15]([C:14]#[N:18])[C:16]#[N:17])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 517165Ammonium AcetateHCID 11206130HCID 11206130, compound

Product 1

HCID 86648061HCID 86648061, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 38.1 (740 mg, 4.13 mmol) and malononitrile (0.275 mL, 4.96 mmol) in toluene (10.0 mL), was added ammonium acetate (79.6 mg, 1.03 mmol) followed by acetic acid (0.284 mL, 4.96 mmol). The resulting mixture was heated at reflux at 140° C. with a Dean-Stark trap for 18 hours. The reaction was concentrated under reduced pressure, and the residue was purified by medium pressure chromatography to yield 38.2 (260 mg, 27% yield). MS ESI (neg.) m/e: 227.1 (M−H)−.

Workup

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure chromatography

Sources & evidence

ORD record
ord-ae484092a8dd41d5bd1fdee93085f059
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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