Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 66644209, compound

HRID 2064492Notes

Reaction equation

HRID 2064492 reaction equation
[ClH:1].Cl.[CH:3]1([CH2:6][NH:7][NH2:8])[CH2:5][CH2:4]1.[CH3:9][C:10]([CH3:17])([CH3:16])[C:11](=O)[CH2:12][C:13]#[N:14]>C(O)C>[ClH:1].[C:10]([C:11]1[CH:12]=[C:13]([NH2:14])[N:7]([CH2:6][CH:3]2[CH2:5][CH2:4]2)[N:8]=1)([CH3:17])([CH3:16])[CH3:9]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 43810474(Cyclopropylmethyl)hydrazine--hydrogen chloride (1/2)

Product 1

HCID 66644209HCID 66644209, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 3A (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.7 g, 93 mmol) in ethanol (100 mL) was heated at reflux for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white precipitate was filtered, washed with ether, and dried to yield 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.38 (d, J=7.12 Hz, 2H), 4.80 (br, 2H), 5.53 (s, 1H), 15.5 (br, 1H); MS (DCI) m/z 194 [M+H]+.

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate (20 mL)
  4. filtrationThe resulting white precipitate was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-4d526d2f3e5b4c10b6c19efaa06d0e9a
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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