Cyanogen Bromide → [(4-Bromophenyl)methyl]cyanamide

HRID 1993972Notes

Reaction equation

HRID 1993972 reaction equation
[N:1]#CBr.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]2C=CC=CC=2)=[CH:7][CH:6]=1>CCOCC>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]#[N:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 12452126HCID 12452126, compound

Product 1

HCID 62483278[(4-Bromophenyl)methyl]cyanamideYield 31.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of cyanogen bromide (3.18 g, 30 mmol), and (4-bromophenyl)methyl aniline (11.25 g, 61 mmol) in ether (50 mL) was stirred for 3 days under nitrogen. The mixture was filtered, the filtrate evaporated, and the residue flash chromatographed on silica gel using 9/1 Hexane/acetone to give (4-bromophenyl)methylcyanamide (2 g, 16%).

Workup

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

Sources & evidence

ORD record
ord-0aec006a692542f3a0e082cb5953acce
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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