Triethylamine → 2-Cyano-1-(3-thienylmethyl)-1H-imidazole

HRID 1193567Notes

Reaction equation

HRID 1193567 reaction equation
[N:1]#[C:2]Cl.[S:4]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:5]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(#N)C>[C:2]([C:11]1[N:10]([CH2:9][C:6]2[CH:7]=[CH:8][S:4][CH:5]=2)[CH:14]=[CH:13][N:12]=1)#[N:1]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10477Cyanogen ChlorideHCID 516892Sodium BicarbonateHCID 212726231-(3-Thienylmethyl)-1H-imidazole

Product 1

HCID 212726242-Cyano-1-(3-thienylmethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-20 °C

Procedure

In a 250 ml, 4-neck flask equipped with a nitrogen bubbler, gas inlet tube, thermometer and septum, add 100 ml acetonitrile and bubble cyanogen chloride (15 g, 0.24 mol) into the acetonitrile. Cool the solution in an ice bath and add 8.2 (0.05 mol) 1-(3-thienylmethyl)-1H-imidazole. After the colorless solution turns yellow-orange and about 1 hour after an orange precipitate forms, cool the slurry to -20° C., slowly add 42 ml (0.3 mol) of triethylamine, holding the temperature below 0° C. After 1 hour at room temperature, pour the reaction onto 600 ml saturated NaHCO3 and extract with ether (3×150 ml). Dry and combine organic layers to obtain tan oil. The oil is purified via Kugelrohr distillation to obtain a colorless oil.

Workup

  1. customIn a 250 ml, 4-neck flask equipped with a nitrogen bubbler, gas inlet tube
  2. temperatureCool the solution in an ice bath
  3. customthe temperature below 0° C
  4. waitAfter 1 hour at room temperature
  5. additionpour
  6. extractionextract with ether (3×150 ml)
  7. customDry
  8. customto obtain tan oil
  9. distillationThe oil is purified via Kugelrohr distillation
  10. customto obtain a colorless oil

Sources & evidence

ORD record
ord-3fa18ceb952d4846b7683eb94ee1cc2e
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

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