Triphosgene → 4-isocyanato-1H-indole

HRID 887216Notes

Reaction equation

HRID 887216 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)=[C:12]=[O:14]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 5834314-Aminoindole

Product 1

HCID 220326444-isocyanato-1H-indoleYield 187.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Aminoindole (0.5 g, 3.78 mmol) in toluene (50 mL) was treated with triphosgene (0.4 g, 1.35 mmol) and heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in diethyl ether, filtered, and the filtrate was concentrated under reduced pressure to provide title compound as yellow oil (0.4 g). 1H NMR (300 MHz, CDCl3-d6) δ 6.62 (m, 1H), 6.84 (d, 1H), 7.1 (t, 1H), 7.23 (m, 2H), 8.3 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d639089c3354e7595e242221ce7fef4
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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