Water → N-[2-(4-bromophenyl)ethyl]formamide

HRID 1954412Notes

Reaction equation

HRID 1954412 reaction equation
Br.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[CH:12](OCC)=[O:13].C(N(CC)CC)C.O>C(OCC)(=O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][CH:12]=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 8471TriethylamineHCID 27570904-Bromophenethylamine hydrobromide

Product 1

HCID 23296214N-[2-(4-bromophenyl)ethyl]formamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

500 g (1.78 mol) of 2-(4-Bromo-phenyl)ethylamine hydrobromide, 1 liter (12.4 mol) of ethyl formate and 248 mL (1.78 mol) of triethylamine were combined and heated to reflux for 3 hrs. The reaction was treated with 1 liter each of deionized water and ethyl acetate. The organic layer was separated and washed with 1 liter each of water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to yield 378 g of a solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hrs
  3. customThe organic layer was separated
  4. washwashed with 1 liter each of water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-074a6603604648fdbd68e1a430e7520a
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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