Hydrochloric Acid → N-(2-Fluoro-6-(trifluoromethyl)benzyl)urea

HRID 28492Notes

Reaction equation

HRID 28492 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH2:4][NH2:5].[NH2:14][C:15](N)=[O:16].Cl>O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:3]=1[CH2:4][NH:5][C:15]([NH2:14])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2774790(2-Fluoro-6-(trifluoromethyl)phenyl)methanamine

Product 1

HCID 22037856N-(2-Fluoro-6-(trifluoromethyl)benzyl)ureaYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-fluoro-6-(trifluoromethyl)benzylamine 1a (51.5 g, 0.267 mmol) in a flask, urea (64 g, 1.07 mmol), HCl (conc., 30.9 mmol, 0.374 mmol) and water (111 mL) were added. The mixture was refluxed for 6 hours. The mixture was cooled to ambient temperature, further cooled with ice and filtered to give a yellow solid. Recrystallization with 400 mL of EtOAc gave 1b as a white solid (46.2 g, 0.196 mmol). MS (CI) m/z 237.0 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperaturefurther cooled with ice
  3. filtrationfiltered
  4. customto give a yellow solid
  5. customRecrystallization with 400 mL of EtOAc

Sources & evidence

ORD record
ord-2cd9d6280f2f41fb97d729b9e41f80eb
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Reaction notes

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