Benzoyl Peroxide → N-{[3-(Bromomethyl)thiophen-2-yl]methyl}acetamide

HRID 1973344Notes

Reaction equation

HRID 1973344 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([NH:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH2:11][Br:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21452353N-[(3-Methylthiophen-2-yl)methyl]acetamide

Product 1

HCID 20311374N-{[3-(Bromomethyl)thiophen-2-yl]methyl}acetamide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Acetyl-2-aminomethyl-3-methylthiophene is dissolved in carbon tetrachloride and treated with an equimolar amount of N-bromosuccinimide and a catalytic amount of dibenzoyl peroxide. The mixture is heated to reflux for 3 hours while irradiating with a 250 watt light. The mixture is cooled and the precipitated succinimide removed by filtration. The filtrate is washed with saturated sodium bisulphite solution, dried over magnesium sulfate and evaporated to yield the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hours
  3. customwhile irradiating with a 250 watt light
  4. temperatureThe mixture is cooled
  5. customthe precipitated succinimide removed by filtration
  6. washThe filtrate is washed with saturated sodium bisulphite solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-e1a77dd5dacc4e2cbfe90ad4c57ba23f
Source dataset
uspto-grants-1976_12
Patent number
US03997527

Reaction notes

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