Cyanogen Bromide → 4-bromophenylcyanamide

HRID 1993957Notes

Reaction equation

HRID 1993957 reaction equation
[N:1]#[C:2]Br.[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7](C)[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 114234-Bromo-2-methylaniline

Product 1

HCID 122959414-bromophenylcyanamideYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-methylaniline (Aldrich Chemical Company) (19.15 g, 103.4 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The reaction was filtered, and the filtrate was concentrated in vacuo at room temperature to give 4-bromophenylcyanamide (8.5 g, 92%) as an off white solid. HRMS: calcd for C8H7BrN2, 209.97926; found (EI, M+), 209.9788.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-2063e9d2f9364e4a9bf51dea535c9343
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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