3-(Trifluoromethyl)aniline → HCID 178512251, compound

HRID 1857471Notes

Reaction equation

HRID 1857471 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](OC2C=CC=CC=2)=[N:20][C:21]#[N:22])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:6][C:19](=[N:20][C:21]#[N:22])[O:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 178512251HCID 178512251, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-trifluoromethylaniline (11 mmol, 1.37 ml) in dichloromethane (25 ml), diphenylcyanocarbonimidate (10 mmol, 2.38 g), and triethylamine (11 mmol, 1.53 ml) were added. The mixture was stirred under nitrogen for 23 h. After concentration the residue was stirred with water, the water was decanted followed by concentration. The residue was stirred with toluene and the solid was collected by filtration giving 1.42 g of N-(3-trifluoromethylphenyl)-N'-cyano-O-phenylisourea (50%);

Workup

  1. concentrationAfter concentration the residue
  2. stirringwas stirred with water
  3. customthe water was decanted
  4. concentrationfollowed by concentration
  5. stirringThe residue was stirred with toluene
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-a1469f1b27474468ba5a3c8495436d23
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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