Phosgene → 2,5-Bis(2,2,2-trifluoroethoxy)phenyl isocyanate

HRID 2412334Notes

Reaction equation

HRID 2412334 reaction equation
[C:1](Cl)(Cl)=[O:2].[F:5][C:6]([F:23])([F:22])[CH2:7][O:8][C:9]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:12][C:10]=1[NH2:11]>C1(C)C=CC=CC=1>[F:5][C:6]([F:22])([F:23])[CH2:7][O:8][C:9]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]([F:21])([F:19])[F:20])=[CH:12][C:10]=1[N:11]=[C:1]=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 133704342,5-Bis(trifluoroethoxy)aniline

Product 1

HCID 133704362,5-Bis(2,2,2-trifluoroethoxy)phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a cooled (15°-20° C.) solution of 67.6 g. (0.684 mole) of phosgene in 250 ml. of toluene is added dropwise over one hour a solution of 49.5 g. (0.171 mole) of 2,5-bis-(2,2,2-trifluoroethoxy)aniline in 350 ml. of toluene. After addition is complete, stirring is continued for 30 minutes, then the mixture is heated to its reflux temperature and maintained at reflux for 30 minutes. The solution is evaporated to provide a liquid residue which gradually crystallizes. The solid is recrystallized from heptane to provide 2,5-bis(2,2,2-trifluoroethoxy)phenyl isocyanate as a white solid, m.p. 50°-52° C.

Workup

  1. temperatureTo a cooled (15°-20° C.) solution of 67.6 g
  2. additionAfter addition
  3. temperaturethe mixture is heated to its
  4. temperaturereflux temperature
  5. temperaturemaintained
  6. temperatureat reflux for 30 minutes
  7. customThe solution is evaporated
  8. customto provide a liquid residue which
  9. customgradually crystallizes
  10. customThe solid is recrystallized from heptane

Sources & evidence

ORD record
ord-75d59ab1fb9741a2aec2b42cc7cfaba8
Source dataset
uspto-grants-1985_01
Patent number
US04491584

Reaction notes

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