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

HRID 1071645Notes

Reaction equation

HRID 1071645 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].Br[CH:10]([CH3:12])[CH3:11].[OH-].[K+].O>CS(C)=O>[CH3:11][CH:10]([CH3:12])[CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 728802-Thienylacetonitrile

Product 1

HCID 123819863-Methyl-2-(2-thienyl)butanenitrileYield 72.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

47.6 g (0.39 mol) of 2-thiopheneacetonitrile and 57.0 g (0.46 mol) of 2-bromopropane were dissolved in 100 ml of DMSO, and a 50% KOH aqueous solution was added dropwise to the solution. After completion of the reaction, water was added, and the mixture was extracted with toluene. After washing with brine and an aqueous saturated ammonium chloride, the mixture was dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to distillation under a reduced pressure (2 to 3 mmHg: 132 to 137 deg), to give 46.4 g (0.28 mol, 72.7%) of the title compound as a colorless oil. The physico-chemical data of the compound was as below.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with toluene
  3. washAfter washing with brine
  4. dry with materialan aqueous saturated ammonium chloride, the mixture was dried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product
  7. distillationThe crude product was subjected to distillation under a reduced pressure (2 to 3 mmHg: 132 to 137 deg)

Sources & evidence

ORD record
ord-e09c4fb7cb8d4dc2bd3c0395967305c7
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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