Styrene → HCID 21224883, compound

HRID 583196Notes

Reaction equation

HRID 583196 reaction equation
[Br:1]N1C(=O)CCC1=O.[N:9]#[C:10][NH2:11].[CH2:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[Br:1][CH2:12][CH:13]([NH:9][C:10]#[N:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 9864CyanamideHCID 67184N-bromobutanimide

Product 1

HCID 21224883HCID 21224883, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-bromosuccinimide (10.68 g, 0.06 mol) and cyanamide (4.2 g, 0.1 mol) were dissolved in 150 m of dichloromethane and the mixture was stirred for 5 min. To this mixture was added a solution of styrene (5.2 g, 0.05 mol) in 20 m of dichloromethane using a dropping funnel for one hour. The resulting reaction mixture was stirred at room temperature for 12 hours, washed with an equal volume of 5% sodium thiosulfate and brine which were freshly prepared, dried over anhydrous magnesium sulfate, concentrated, and then purified by silica gel column chromatography (eluent:ethylacetate/toluene=1/20, v/v) to afford 8.98 g of 2-bromo-1-phenylethyl cyanamide.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 12 hours
  3. washwashed with an equal volume of 5% sodium thiosulfate and brine which
  4. customwere freshly prepared
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-ca8f9422d7814c70908e5b704cffe1b0
Source dataset
uspto-grants-1999_07
Patent number
US05929103

Reaction notes

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