p-(Trifluoromethoxy)phenyl isocyanate → HCID 13251606, compound

HRID 484756Notes

Reaction equation

HRID 484756 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19]>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([NH:20][C:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)=[O:12])=[O:19]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 27735902-Chloro-5-fluorobenzamide

Product 1

HCID 13251606HCID 13251606, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4.06 g (0.02 mol) of 4-trifluoromethoxy-phenyl isocyanate in 10 ml of dry toluene is added to 3.48 g (0.02 mol) of 2-chloro-5-fluorobenzamide in 100 ml of dry toluene, at 100° C., in the absence of moisture. The mixture is boiled under reflux for 10 hours. After it has been cooled, the precipitated product is filtered off under suction and rinsed with methanol. 6.2 g (82.5% of theory) of 1-(2-chloro-5-fluoro-benzoyl)-3-(4-trifluoromethoxyphenyl)-urea of melting point 199° C. are obtained. The compound is identical to the compound prepared by process variant (a).

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureAfter it has been cooled
  3. filtrationthe precipitated product is filtered off under suction
  4. washrinsed with methanol

Sources & evidence

ORD record
ord-19caac0bce364949b4db713e54d75940
Source dataset
uspto-grants-1985_08
Patent number
US04533676

Reaction notes

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