Carbonyl fluoride → [4-(Trifluoromethyl)phenyl]carbamyl fluoride

HRID 1979630Notes

Reaction equation

HRID 1979630 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].F.C(F)([F:17])=O.CCCCCCCCCCCCCCC.FC(F)(F)C1C=CC(N)=CC=1>>[F:13][C:10]([F:11])([F:12])[C:7]1[CH:6]=[CH:5][C:4]([NH:1][C:2]([F:17])=[O:3])=[CH:9][CH:8]=1

Participants

7

Reactant 6

HCID 9623Carbonyl fluorideHCID 99644-(Trifluoromethyl)anilineHCID 12391PentadecaneHCID 14917Hydrofluoric AcidHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178506046HCID 178506046, compound

Product 1

HCID 15544765[4-(Trifluoromethyl)phenyl]carbamyl fluoride

Conditions

Temperature
24 °C

Procedure

4-(Trifluoromethyl)phenyl carbamic fluoride was prepared in situ by the reaction of 224 parts of 1-isocyanato-4-(trifluoromethyl)benzene and 460 parts of hydrogen fluoride added over a period of about 35 minutes at about 3° C. The reaction mixture was then sealed in a polytetrafluoroethylene reaction vessel, heated to about 24° C., and maintained thereat, with agitation, for about 112 hours. Infra-red analysis of the gaseous phase, when the reaction vessel was opened to atmospheric pressure, indicated large quantities of carbonyl fluoride present. The remaining organic product was analyzed by gas chromatographic techniques, using n-pentadecane as an internal standard, indicating a yield of 114 parts of 4-(trifluoromethyl)benzenamine.

Workup

  1. additionadded over a period of about 35 minutes at about 3° C
  2. temperaturemaintained

Sources & evidence

ORD record
ord-fa1ee8384f1945818a8ab9cca74db8c7
Source dataset
uspto-grants-1984_11
Patent number
US04481370

Reaction notes

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