Toluene → 3-(Trifluoromethyl)phenyl isocyanate

HRID 1968941Notes

Reaction equation

HRID 1968941 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.C1(C)C=CC=CC=1.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>ClCCl>[N:25]([C:24]1[CH:26]=[CH:27][CH:28]=[C:22]([C:21]([F:20])([F:29])[F:30])[CH:23]=1)=[C:5]=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73753-(Trifluoromethyl)anilineHCID 94429Triphosgene

Product 1

HCID 94833-(Trifluoromethyl)phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (0.75 g) was added to anhydroue toluene (10 ml) under nitrogen protection, and then a solution of 3-trifluoromethylaniline (0.8 g) in dichloromethane (15 ml) was added dropwise in an ice-bath. After addition, the reaction mixture was stirred at room temperature for 15 min, and then heated to 80° C. for 6 h. The completion of the reaction was indicated by TLC. The reaction mixture was concentrated under reduced pressure to give the product as oil, which then was solidified.

Workup

  1. additionAfter addition
  2. temperatureheated to 80° C. for 6 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f94599ab5229487a92bffb8a9e3291ba
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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