Triethylamine → (4-Ethyl-1,3-thiazol-2-yl)acetonitrile

HRID 2375314Notes

Reaction equation

HRID 2375314 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH3:5].[C:7]([CH2:9][C:10]([NH2:12])=[S:11])#[N:8].C(N(CC)CC)C>CCO>[CH2:4]([C:3]1[N:12]=[C:10]([CH2:9][C:7]#[N:8])[S:11][CH:2]=1)[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131561-Bromo-2-butanoneHCID 14162772-Cyanoethanethioamide

Product 1

HCID 11701070(4-Ethyl-1,3-thiazol-2-yl)acetonitrileYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-bromo-2-butanone (10.3 g, 57.98 mmol) in EtOH (200 mL) were added 2-cyanothioacetamide (5.8 g, 57.98 mmol) and triethylamine (1.59 mL, 11.6 mmol) and the solution was stirred under reflux for 1 h. After cooling down to r.t., the solvent was removed. The orange solid obtained was washed with AcOEt then cyclohexane, and recrystallized from EtOH to afford 7.2 g of the title compound as orange needles (Y=81%).

Workup

  1. temperatureunder reflux for 1 h
  2. customthe solvent was removed
  3. customThe orange solid obtained
  4. washwas washed with AcOEt
  5. customcyclohexane, and recrystallized from EtOH

Sources & evidence

ORD record
ord-4d7fa44a3fae490a8bc142800f35428d
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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