Triethylamine → 1-(2-Thienyl)propyl isocyanide

HRID 1708973Notes

Reaction equation

HRID 1708973 reaction equation
C(N(CC)CC)C.[CH:8]([NH:10][CH:11]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[CH2:12][CH3:13])=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[S:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH:11]([N+:10]#[C-:8])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 148354442-(1-Formylaminopropyl) thiophene

Product 1

HCID 152885881-(2-Thienyl)propyl isocyanideYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

231 g of triethylamine are added to a solution of 96.5 g of 2-(1-formylaminopropyl) thiophene in 500 ml of methylene chloride and the mixture is cooled at below -30° C. 105 g of phosphorus oxychloride are added dropwise to the mixture at below -30° to -20° C. and and the mixture is stirred at the same temperature for 1 hour. After the reaction, the mixture is poured into 1 litter of an aqueous 10% potassium carbonate solution. The aqueous mixture is stirred at room temperature for 1 hour and the methylene chloride layer is separated therefrom. Said methylene chloride layer is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 74.5 g of 1-(2-thienyl)propyl isocyanide as a colorless oil.

Workup

  1. temperaturethe mixture is cooled at below -30° C
  2. customAfter the reaction
  3. stirringThe aqueous mixture is stirred at room temperature for 1 hour
  4. customthe methylene chloride layer is separated
  5. washis washed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-be998bdbb08141de8764b58e892ed2c4
Source dataset
uspto-grants-1990_08
Patent number
US04946862

Reaction notes

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