3-(Trifluoromethyl)aniline → N,N'-Di-(m-trifluoromethylphenyl)urea

HRID 1243646Notes

Reaction equation

HRID 1243646 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]=[C:10]=[O:11])[CH:4]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>ClCCl>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 94833-(Trifluoromethyl)phenyl isocyanate

Product 1

HCID 136250N,N'-Di-(m-trifluoromethylphenyl)ureaYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask under nitrogen, α,α,α-trifluro-m-tolyl isocyanate (3 g, 16 mmol) was dissolved in anhydrous dichloromethane (40 mL). 3-(Trifluoromethyl) aniline (2 g, 12.4 mmol) was added through a syringe at room temperature. A precipitate was formed 15 minutes after the completion of the addition. The reaction was left to stir overnight at room temperature. The next day the white solid was collected by filtration, washed with dichloromethane and dried. This solid corresponds to the desired urea. (4.2 g, 97% yield). 1H NMR (400 MHz, DMSO) δ 7.35 (d, 2H), 7.55 (m, 2 H), 7.6 (d, 2H), 8.05 (s, 2H). MS calculated=m/e 348, found=m/e 348.

Workup

  1. customA precipitate was formed 15 minutes
  2. additionafter the completion of the addition
  3. waitThe reaction was left
  4. filtrationThe next day the white solid was collected by filtration
  5. washwashed with dichloromethane
  6. customdried

Sources & evidence

ORD record
ord-06aa03ec397f43fa9e11421b67188a10
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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