2-Bromopropane → 3-Methyl-2-(2-thienyl)butanenitrile

HRID 1582769Notes

Reaction equation

HRID 1582769 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].[NH2-].[Na+].Br[CH:12]([CH3:14])[CH3:13].[Cl-].[NH4+]>O1CCCC1>[CH3:13][CH:12]([CH3:14])[CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 24533Sodium amideHCID 25517Ammonium ChlorideHCID 728802-Thienylacetonitrile

Product 1

HCID 123819863-Methyl-2-(2-thienyl)butanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2-Thienyl acetonitrile, 15 g 0.12 mol, was dissolved in tetrahydrofuran 125 ml and added dropwise to a suspension of sodium amide 4.75 g 0.12 mol in tetrahydrofuran 250 ml under ice-cooling. After stirring for 5 minutes, a solution of 2-bromopropane 11.4 ml 0.12 mol in tetrahydrofuran 125 ml was added dropwise thereto. Aqueous saturated ammonium chloride was added to the reaction mixture which was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 5.56 g 33.6 mmol, 28.0% was obtained as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound
  7. custom5.56 g 33.6 mmol, 28.0% was obtained as a yellow oil

Sources & evidence

ORD record
ord-bbb614001b2943399423b6ff4f3f8f04
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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