Triethylamine → 1-(Isocyanatomethyl)-2,4-dimethoxybenzene

HRID 2098290

Reaction equation

HRID 2098290 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11]C(O)=O.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:17]=[C:20]=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3505552-(2,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 112525271-(Isocyanatomethyl)-2,4-dimethoxybenzeneYield 298.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2,4-dimethoxyphenylacetic acid (3.92 g, 20 mmol) in dry toluene (100 mL) was added dry triethylamine (2.93 mL, 4.2 mmol) and diphenyl phosphorylazide (4.31 mL, 4 mmol). The 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 2,4-dimethoxybenzyl isocyanate (2.31 g, 60%). IR vmax/cm−1 2243.

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-c9186fe9548543bcab9fdbcfa277e52e
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Linked notes

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