2,6-Difluorobenzoyl isocyanate → N-(((2,5-dichloro-4-(2-chloro-1,1,2-trifluoroethoxy)phenyl)amino)carbonyl)2,6-difluorobenzamide

HRID 463454Notes

Reaction equation

HRID 463454 reaction equation
[Cl:1][CH:2]([F:16])[C:3]([F:15])([F:14])[O:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH2:12])=[C:7]([Cl:13])[CH:6]=1.[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[C:20]([N:22]=[C:23]=[O:24])=[O:21]>C1(C)C=CC=CC=1>[Cl:13][C:7]1[CH:6]=[C:5]([O:4][C:3]([F:15])([F:14])[CH:2]([Cl:1])[F:16])[C:10]([Cl:11])=[CH:9][C:8]=1[NH:12][C:23]([NH:22][C:20](=[O:21])[C:19]1[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:18]=1[F:17])=[O:24]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 135172904-(2-Chloro-1,1,2-trifluoroethoxy)-2,5-dichlorobenzenamine

Product 1

HCID 13517292N-(((2,5-dichloro-4-(2-chloro-1,1,2-trifluoroethoxy)phenyl)amino)carbonyl)2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.9 g (0.02 mole) of the above prepared 4-(2-chloro-1,1,2-trifluoroethoxy)-2,5-dichlorobenzeneamine in 100 ml toluene was placed in a 500 ml 3-necked round bottom flask fitted with a mechanical stirrer, thermometer and reflux condenser and 5.5 g (0.03 mole) of 2,6-difluorobenzoyl isocyanate was added while stirring. The temperature rose from 23° to 34° C. in a few minutes. The mixture was heated under reflux while stirring for one hour giving a clear solution which was cooled in an ice water bath. The toluene was removed by evaporation in a rotary evaporator and 25 ml acetic acid and 5 ml water were added to the residue. The resulting mixture was heated to boiling, giving a clear solution, cooled in an ice water bath and suction filtered. The filter cake obtained was washed with a little cold aqueous acetic acid and dried at room temperature. Weight, 8.5 g of white solid. m.p. 177°-179° C. The structure was verified by NMR.

Workup

  1. customwas placed in a 500 ml 3-necked round bottom flask
  2. customfitted with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. waitThe temperature rose from 23° to 34° C. in a few minutes
  5. temperatureThe mixture was heated
  6. temperatureunder reflux
  7. stirringwhile stirring for one hour
  8. customgiving a clear solution which
  9. temperaturewas cooled in an ice water bath
  10. customThe toluene was removed by evaporation in a rotary evaporator and 25 ml acetic acid and 5 ml water
  11. additionwere added to the residue
  12. temperatureThe resulting mixture was heated
  13. customgiving a clear solution
  14. temperaturecooled in an ice water bath
  15. filtrationsuction filtered
  16. customThe filter cake obtained
  17. washwas washed with a little cold aqueous acetic acid
  18. customdried at room temperature

Sources & evidence

ORD record
ord-2694f2368b2c4eb2a7bc832f50604659
Source dataset
uspto-grants-1985_05
Patent number
US04518804

Reaction notes

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