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

HRID 413747

Reaction equation

HRID 413747 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-7d40f5e34296423c91a8780b334a3abe
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Linked notes

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