Hydrochloric Acid → Ethyl (4-chlorobenzyl)carbamate

HRID 495625

Reaction equation

HRID 495625 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:11](=[O:12])[O:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 660364-Chlorobenzylamine

Product 1

HCID 874364Ethyl (4-chlorobenzyl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chlorobenzylamine (1.0556 g) was dissolved in pyridine (5 ml), and to the solution was added dropwise ethyl chloroformate.(0.855 ml) during 5 minutes under ice-cooling. After the mixture was stirred for 3 hours, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (1.562 g, 98%).

Workup

  1. temperature(0.855 ml) during 5 minutes under ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution
  4. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8537c4556af84daa82eae7dfe7af07d9
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Linked notes

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