3-(Trifluoromethyl)phenyl isocyanate → 3-(Trifluoromethyl)phenyl carbamic fluoride

HRID 1979627Notes

Reaction equation

HRID 1979627 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[C:2]=[O:3].F.C(F)([F:17])=O>>[F:13][C:10]([F:11])([F:12])[C:6]1[CH:5]=[C:4]([NH:1][C:2]([F:17])=[O:3])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 9623Carbonyl fluorideHCID 14917Hydrofluoric Acid2×HCID 178506046HCID 178506046, compound

Product 1

HCID 204396133-(Trifluoromethyl)phenyl carbamic fluoride

Conditions

Temperature
24 °C

Procedure

3-(Trifluoromethyl)phenyl carbamic fluoride was prepared in situ by the reaction of 187 parts of 1-isocyanato-3-(trifluoromethyl)benzene and 370 parts of hydrogen fluoride added over a period of about 15 minutes at about 4° C. The reaction mixture was then sealed in a polytetrafluoroethylene reaction vessel, heated to about 24° C., and maintained thereat, with agitation, for about 96 hours. The reaction vessel was then opened to atmospheric pressure and most of the hydrogen fluoride and carbonyl fluoride gases removed. The remaining organic product was analyzed by gas chromatographic techniques, using n-pentadecane as an internal standard, indicating a yield of 41 parts of 3-(trifluoromethyl)benzenamine.

Workup

  1. additionadded over a period of about 15 minutes at about 4° C
  2. temperaturemaintained
  3. customremoved

Sources & evidence

ORD record
ord-5d60a0c9f7294859ab4becaba6436242
Source dataset
uspto-grants-1984_11
Patent number
US04481370

Reaction notes

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