Potassium Cyanide → Methyl 5-(cyanomethyl)thiophene-3-carboxylate

HRID 900993Notes

Reaction equation

HRID 900993 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13]Cl)[S:10][CH:9]=1)=[O:7]>CN(C=O)C.[Na+].[Cl-]>[CH3:4][O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][C:1]#[N:2])[S:10][CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 12926494Methyl 5-(chloromethyl)thiophene-3-carboxylate

Product 1

HCID 57750761Methyl 5-(cyanomethyl)thiophene-3-carboxylateYield 105.1%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of potassium cyanide (3.2 g, 48.5 mmol) in DMF (25 mL) is treated with 5-chloromethyl-thiophene-3-carboxylic acid methyl ester (4.4 g, 23.1 mmol) in DMF (30 mL). After stirring for 14 h at room temperature the mixture is warmed to 50° C. for 0.5 h. After cooling, the solution is diluted with saturated aq NaCl and extracted with CHCl3 (3×). The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo to give 5-cyanomethyl-thiophene-3-carboxylic acid methyl ester (4.4 g, 100%). 1H NMR (CDCl3, 300 MHz) δ 8.00 (s, 1 H), 7.44 (s, 1 H), 3.90 (s, 2 H), 3.84 (s, 3 H).

Workup

  1. temperatureis warmed to 50° C. for 0.5 h
  2. temperatureAfter cooling
  3. extractionextracted with CHCl3 (3×)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d8684ab69fc43acbc77495cc47f80c1
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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