3-(Trifluoromethyl)aniline → 3-(Trifluoromethyl)phenylcyanamide

HRID 636685Notes

Reaction equation

HRID 636685 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[N:12]#[C:13]Br>C(OCC)C>[NH:1]([C:2]1[CH:3]=[C:4]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:6][CH:7]=1)[C:13]#[N:12]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 10476Cyanogen Bromide

Product 1

HCID 110741023-(Trifluoromethyl)phenylcyanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-aminobenzotrifluoride (15.0 g, 93.1 mmol), cyanogen bromide (12.2 g, 129 mmol) and diethyl ether was stirred at reflux for 40 h. The crude mixture was purified by chromatography using silica gel and a mixture of petroleum ether and dichloromethane as eluent (1:1). The product was isolated as the free base. Yield 5.2 g, 25%.

Workup

  1. temperatureat reflux for 40 h
  2. customThe crude mixture was purified by chromatography
  3. additiona mixture of petroleum ether and dichloromethane as eluent (1:1)
  4. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-4e8c65036805420582fd5cba8493c7ce
Source dataset
uspto-grants-2001_02
Patent number
US06194447B1

Reaction notes

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