Cyanogen Bromide → (4-Bromo-3-methylphenyl)cyanamide

HRID 1993970Notes

Reaction equation

HRID 1993970 reaction equation
[N:1]#[C:2]Br.[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[CH3:12]>C(OCC)C.C1COCC1>[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:2]#[N:1])=[CH:7][C:6]=1[CH3:12]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 233594-Bromo-3-methylaniline

Product 1

HCID 62483486(4-Bromo-3-methylphenyl)cyanamideYield 26.4%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

A mixture of cyanogen bromide (0.550 g, 5.19 mmol), and (4-bromo-3-methylaniline (2.04 g, 11 mmol) (Aldrich Chemical Company) in diethyl ether/THF (8 mL) was stirred for 3 days under nitrogen. The reaction was filtered, the filtrate evaporated, and the residue flash chromatographed on silica gel using 9/1 Hexane/acetone to give (4-bromo-3-methylphenyl)cyanamide (0.289 g, 13%). HRMS: calcd for 2 C8H7BrN2+H+, 420.96579; found (ESI-FT/MS, [2M+H]+), 420.966.

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated
  3. customthe residue flash chromatographed on silica gel using 9/1 Hexane/acetone

Sources & evidence

ORD record
ord-4ce47e76ec574117828e7dde1d796f0e
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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