Acetic Acid → HCID 59520485, compound

HRID 1162776Notes

Reaction equation

HRID 1162776 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH2:7][CH2:8][OH:9])=[O:5])#[N:2].[C:10]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1.O>[C:1]([C:3](=[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:4]([NH:6][CH2:7][CH2:8][OH:9])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 517165Ammonium AcetateHCID 51527282-cyano-N-(2-hydroxyethyl)acetamide

Product 1

HCID 59520485HCID 59520485, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Cyano-N-(2-hydroxyethyl)acetamide (4.62 g, 36.1 mmol), cyclohexanone (3.89 g, 4.10 mL, 39.7 mmol), acetic acid (0.433 g, 0.413 mL, 7.21 mmol) and ammonium acetate (2.78 g, 36.1 mmol) were suspended in toluene (150 mL) and the mixture heated to reflux under Dean-Stark conditions until no more water was collected (˜1.5 h). The mixture was concentrated to remove toluene before partitioning between EtOAc/Water. The organic phase was collected, dried and concentrated to a lower volume before addition of small quantities of heptane. The glass was etched until precipitation occurred and the solid collected by filtration. The desired product was isolated in 3 batches (4.2 g, 20.2 mmol, 56%). The sample was used directly in the next step without any further purification.

Workup

  1. temperaturethe mixture heated
  2. customwas collected (˜1.5 h)
  3. concentrationThe mixture was concentrated
  4. customto remove toluene
  5. custombefore partitioning between EtOAc/Water
  6. customThe organic phase was collected
  7. customdried
  8. concentrationconcentrated to a lower volume before addition of small quantities of heptane
  9. customThe glass was etched until precipitation
  10. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-44fb24f84a06491fb87d12c61a5800d8
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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