Water → (2-Methyl-1,3-thiazol-4-yl)acetonitrile

HRID 636647Notes

Reaction equation

HRID 636647 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1.[C-:10]#[N:11].[K+].O>C(=O)(O)[O-].[Na+].CCOC(C)=O>[C:10]([CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1)#[N:11]

Participants

6

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)

Product 1

HCID 2320580(2-Methyl-1,3-thiazol-4-yl)acetonitrileYield 24.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-Chloromethyl-2-methyl thiazole hydrochloride (1 g, 5.4 mmol) was taken up in sodium bicarbonate saturated aqueous solution and extracted with EtOAc, dried (MgSO4), and concentrated in vacuo. The residue was dissolved in 95% ethanol (50 mL) and potassium cyanide (353 mg, 5.4 mmol) followed by water (5 mL) were added to the reaction mixture. The mixture was refluxed for 18 hours and cooled to room temperature. The reaction mixture was taken up in EtOAc and washed with water, dried (MgSO4), and concentrated in vacuo. The residue was purified on silica with a gradient of heptane to 1:1 heptane/EtOAc to give 4-cyanomethyl-2-methyl thiazole (180 mg, 24%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 95% ethanol (50 mL)
  5. additionwere added to the reaction mixture
  6. temperatureThe mixture was refluxed for 18 hours
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on silica with a gradient of heptane to 1:1 heptane/EtOAc

Sources & evidence

ORD record
ord-8ebb3a5cefef410ba6292c6b22bf930f
Source dataset
uspto-grants-2001_02
Patent number
US06194437B1

Reaction notes

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