3-(Trifluoromethyl)aniline → 1-(2,6-Dichlorobenzoyl)-3-(3-trifluoromethylphenyl)urea

HRID 128145Notes

Reaction equation

HRID 128145 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([NH2:6])=[O:5].C([Li])CCC.Cl[C:18](OC1C=CC([N+]([O-])=O)=CC=1)=[O:19].[NH2:30][C:31]1[CH:32]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:35][CH:36]=1>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([NH:6][C:18]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=1)=[O:19])=[O:5]

Participants

6

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 161832,6-DichlorobenzamideHCID 821294-Nitrophenyl chloroformateHCID 178418339Butyllithium

Product 1

HCID 142764251-(2,6-Dichlorobenzoyl)-3-(3-trifluoromethylphenyl)ureaYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-72 °C

Procedure

A solution of 0.912 grams of 2,6-dichlorobenzamide in 75 ml. of dry tetrahydrofuran was placed in a 3-necked, 250 ml. round bottomed flask. The solution was cooled to about -72° C. with a dry ice/acetone bath. To the mixture was added 1.8 ml. of n-butyllithium solution over a 5-minute period. The mixture was allowed to stand for 30 minutes at -75° C. to -70° C. A solution of 0.804 grams of 4-nitrophenyl chloroformate in 24 ml. of dry tetrahydrofuran was added over a period of 30 minutes at about -72° C. The mixture was allowed to stand an additional 30 minutes in the cold at which time it became colorless. The solution was warmed to -40° C. and held at that temperature for 2.75 hours. The mixture was cooled again to about -72° C. and a solution of 0.64 grams of 3-aminobenzotrifluoride in 25 ml. of dry tetrahydrofuran was added over 10 minutes. The solution was allowed to warm to room temperature and was then heated at 50° C. for 16 hours. The solvent was removed and the residue was dissolved in 10 ml. of ether. The solution was washed with 1 N sodium carbonate solution, dried over magnesium sulfate and the solvent again removed. The residue was triturated under ether to give 0.6 grams of a white crystalline solid melting above 200° C.

Workup

  1. additionTo the mixture was added 1.8 ml
  2. waitto stand an additional 30 minutes in the cold at which time it
  3. temperatureThe solution was warmed to -40° C.
  4. waitheld at that temperature for 2.75 hours
  5. temperatureThe mixture was cooled again to about -72° C.
  6. temperatureto warm to room temperature
  7. temperaturewas then heated at 50° C. for 16 hours
  8. customThe solvent was removed
  9. dissolutionthe residue was dissolved in 10 ml
  10. washThe solution was washed with 1 N sodium carbonate solution
  11. dry with materialdried over magnesium sulfate
  12. customthe solvent again removed
  13. customThe residue was triturated under ether

Sources & evidence

ORD record
ord-2134862da9ca4910a1d3825c00efb2f6
Source dataset
uspto-grants-1981_03
Patent number
USRE030563

Reaction notes

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