p-Toluenesulfonic acid → N-[2-(4-bromophenyl)ethyl]formamide

HRID 540361Notes

Reaction equation

HRID 540361 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH:22](OCC)=[O:23]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][CH:22]=[O:23])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8025Ethyl formateHCID 533915p-Bromophenethylamine

Product 1

HCID 23296214N-[2-(4-bromophenyl)ethyl]formamideYield 100%

Procedure

4-Bromo-phenethylamine (4.45 g, 22.25 mmol) was dissolved in ethyl formate (100 mL). 5 mg of TsOH was added. The clear colorless solution was heated in an oil bath to reflux for 16 h. The reaction solution was cooled to r.t, passed through a short silica gel plug, rinsed with ethyl acetate. The filtrate was evaporated to yield 5.1 g (100%) of the title compound as a liquid which became a solid on standing. MS: 230 (M+H+).

Workup

  1. temperatureThe clear colorless solution was heated in an oil bath
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction solution was cooled
  4. washrinsed with ethyl acetate
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-00f2667d7f3146e09e931fd8a7ddda97
Source dataset
uspto-grants-2014_10
Patent number
US08871788B2

Reaction notes

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