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

HRID 1993968Notes

Reaction equation

HRID 1993968 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[O:12][CH3:13]>CCOCC.C1COCC1>[Br:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:2]#[N:1])=[CH:7][C:6]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 70182544-Bromo-3-methoxyaniline

Product 1

HCID 71423724(4-Bromo-3-methoxyphenyl)cyanamideYield 25.5%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

A mixture of cyanogen bromide (0.550 g, 5.19 mmol) and 4-bromo-3-methoxyaniline (Lancaster Synthesis Inc., P.O. Box 1000, Windham, N.H. 03087-9977) (2.2 g, 11 mmol) in ether/THF (6 mL) was stirred for 3 days under nitrogen atmosphere. 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-methoxyphenyl)cyanamide (0.300 g, 12%). HRMS: calcd for 2 C8H7BrN2O+H+, 452.95562; found (ESI-FT/MS, [2M+H]1+), 452.9556.

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-9fa472209d9a4c5cb157bdc2cd015fdd
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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