Cyanogen Bromide → 4-bromophenylcyanamide

HRID 1993959Notes

Reaction equation

HRID 1993959 reaction equation
[N:1]#[C:2]Br.[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7](CC)[CH:6]=1>C(OCC)C>[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:2]#[N:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 122959414-bromophenylcyanamideYield 24.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-ethylaniline (20.6 g, 103 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The amine hydrobromide was filtered off, and the filtrate was concentrated in vacuo at room temperature and triturated with hexane to give 4-bromophenylcyanamide (2.3 g, 10%) as an off white solid. HRMS: calcd for C9H9BrN2+H+, 225.00218; found (ESI-FTMS, [M+H]+), 225.00277.

Workup

  1. filtrationThe amine hydrobromide was filtered off
  2. concentrationthe filtrate was concentrated in vacuo at room temperature
  3. customtriturated with hexane

Sources & evidence

ORD record
ord-499684658e3744139080ceadd60488cb
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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