Toluene → Benzene, 1-(isocyanatomethyl)-2-(trifluoromethoxy)-

HRID 277778Notes

Reaction equation

HRID 277778 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:30](Cl)(Cl)=[O:31].C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:12])([F:13])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][N:7]=[C:30]=[O:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 88675Proton spongeHCID 2777251(2-(Trifluoromethoxy)phenyl)methanamine

Product 1

HCID 22625932Benzene, 1-(isocyanatomethyl)-2-(trifluoromethoxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a methylene chloride solution of commercially available 2-(trifluoromethoxy)benzyl amine (2.81 mmol) at 0° C. was added solid Proton sponge (2.81 mmol) then a 20% solution of phosgene in toluene (2.81 mmol). The solution was stirred at 25° C. for 1 hour and then washed with 1N HCl (40 mL). The methylene chloride was then dried with sodium sulfate and evaporated. 1H-NMR (CDCl3): 7.5 ppm (d, 1H); 7.4 ppm (m, 2H); 7.3 ppm (d, 1H); 4.6 ppm (s, 2H).

Workup

  1. washwashed with 1N HCl (40 mL)
  2. dry with materialThe methylene chloride was then dried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-f438b684bd954697972d7b27b1597f09
Source dataset
uspto-grants-2002_03
Patent number
US06358956B1

Reaction notes

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