Triethylamine → 2-(Isocyanatomethyl)thiophene

HRID 2098295Notes

Reaction equation

HRID 2098295 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6]C(O)=O.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:12]=[C:15]=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 158906212-(Isocyanatomethyl)thiopheneYield 62.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-thiopheneacetic acid (2.84 g, 20 mmol) in dry toluene (22.5 mL) was added dry triethylamine (2.93 mL, 4.2 mmol) and diphenyl phosphorylazide (4.31 mL, 4 mmol). The reaction mixture was stirred at room temperature for 0.5 hours, and then heated at reflux for a further 3 hours. After cooling, the mixture was concentrated under reduced pressure and purified by distillation using an oil pump to give thiophen-2-ylmethyl isocyanate (0.35 g, 12%) as a colourless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for a further 3 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. distillationpurified by distillation

Sources & evidence

ORD record
ord-08dc485a10f544e69254406ca59069c4
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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