Sodium Hydroxide → 4-Isocyanato-2-(trifluoromethyl)benzonitrile

HRID 1919782Notes

Reaction equation

HRID 1919782 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[OH-].[Na+].[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1>C1(C)C=CC=CC=1.O1CCOCC1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:15]=[C:5]=[O:11])=[CH:17][C:18]=1[C:24]([F:25])([F:26])[F:27])#[N:21]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrileYield 144.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

21.16 g of triphosgene are dissolved in 100 mL of anhydrous toluene in a 500 mL four-neck bottle equipped with a nitrogen intake, a magnetic stirrer, a condenser and a guard filled with 2 N sodium hydroxide. A solution of 20 g of 4-amino-2-trifluoromethylbenzonitrile in 125 mL of anhydrous dioxan is added dropwise at ambient temperature in 1 hour 30 min. The mixture is heated to 110° C. Pronounced release of gas for 1 hour then appearance of an insoluble brown substance. After 2 hours under reflux, stirring is maintained overnight at AT. The insoluble matter is filtered and rinsed with toluene. The filtrate is concentrated in order to obtain 21.8 g of expected product (Yd=96%). The product is stored in solution in THF (2 M) in a refrigerator.

Workup

  1. customequipped with a nitrogen intake, a magnetic stirrer, a condenser
  2. temperatureAfter 2 hours under reflux
  3. temperatureis maintained overnight at AT
  4. filtrationThe insoluble matter is filtered
  5. washrinsed with toluene
  6. concentrationThe filtrate is concentrated in order

Sources & evidence

ORD record
ord-d6e381dbf44847258ae195431a38eaa1
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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