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

HRID 843583Notes

Reaction equation

HRID 843583 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-86ab413ff5aa48bfa2e1eb91acb6a5b2
Source dataset
uspto-grants-2002_04
Patent number
US06380180B1

Reaction notes

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