Citric Acid → methyl N-[1-(3-bromophenyl)ethyl]carbamate

HRID 427253Notes

Reaction equation

HRID 427253 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]([NH2:7])[CH3:6].N1C=CC=CC=1.Cl[C:18]([O:20][CH3:21])=[O:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([NH:7][C:18](=[O:19])[O:20][CH3:21])[CH3:6])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 167857641-(3-Bromophenyl)ethanamine

Product 1

HCID 15483792methyl N-[1-(3-bromophenyl)ethyl]carbamateYield 34.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 23.8 g of 3-bromo-α-methylbenzylamine in toluene (120 ml), 14.1 g of pyridine was added at room temperature. To this solution, 18.6 g of methyl chloroformate was dropwise added under cooling with ice, followed by stirring at room temperature for 2 hours. The reaction solution was poured into a citric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with a citric acid aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 10.5 g of methyl N-[1-(3-bromophenyl)ethyl]carbamate as a colorless transparent viscous liquid.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a citric acid aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9f3808b31a5484d9c9deeeb7c97155d
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

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