Triethylamine → (2-Isocyanatocyclopropyl)benzene

HRID 450966Notes

Reaction equation

HRID 450966 reaction equation
[C:1]1([CH:7]2[CH2:9][CH:8]2C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:15]([CH2:18]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])=CC=1>C1(C)C=CC=CC=1>[N:15]([CH:8]1[CH2:9][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[C:18]=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703232-Phenylcyclopropane-1-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 582709(2-Isocyanatocyclopropyl)benzeneYield 81.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-phenylcyclopropanecarboxylic acid (1.0 g, 6.17 mmol) in dry toluene (20 mL) was added triethylamine (934 mg, 9.26 mmol) and DPPA (2.0 g, 7.41 mmol) under N2, and the reaction mixture was refluxed for 3 h. The solution was concentrated to give (2-isocyanatocyclopropyl)benzene (800 mg), which was used for the next step without further purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-7019917bd13d4f64a7fdaed93ff7742c
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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