4-Chloro-3-(trifluoromethyl)aniline → 1-(4-Chloro-3-(trifluoromethyl)phenyl)urea

HRID 2094776Notes

Reaction equation

HRID 2094776 reaction equation
[O-:1][C:2]#[N:3].[Na+].[F:5][C:6]([F:16])([F:15])[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[Cl:14])[NH2:10]>O.C(O)(=O)C>[Cl:14][C:13]1[CH:12]=[CH:11][C:9]([NH:10][C:2]([NH2:3])=[O:1])=[CH:8][C:7]=1[C:6]([F:5])([F:15])[F:16]

Participants

5

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 517096Sodium Cyanate

Product 1

HCID 179250491-(4-Chloro-3-(trifluoromethyl)phenyl)ureaYield 94.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium cyanate (1.7 g, 0.02 mol) was dissolved in water (17 ml) at room temperature to obtain a clear solution. This solution was then charged drop wise to the clear solution of 3-trifluoromethyl-4-chloro aniline (5 g, 0.025 mol) in acetic acid (25 ml) at 40° C.-45° C. within 1-2 hours. The reaction mass was then agitated for whole day cooling gradually to room temperature. The obtained solid was then filtered, washed with water and vacuum dried at 50° C. to afford (4.5 g) the desired product, i.e., 1-(4-chloro-3-(trifluoromethyl)phenyl)urea.

Workup

  1. customto obtain a clear solution
  2. filtrationThe obtained solid was then filtered
  3. washwashed with water and vacuum
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-83e1f4fec7bf486788fd2907f9a881bc
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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