Ethylamine → phenyl N-ethylcarbamate

HRID 1112603Notes

Reaction equation

HRID 1112603 reaction equation
[CH2:1]([NH2:3])[CH3:2].[OH-].[Na+].Cl[C:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]>C(Cl)Cl>[CH2:1]([NH:3][C:7](=[O:8])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformate

Product 1

HCID 2802346phenyl N-ethylcarbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aqueous solution of ethylamine (2.58g of 70% solution, 0.04 mole) and an aqueous sodium hydroxide solution (1.44g in 8 ml solution, 0.036 mole) were added dropwise simultaneously over a period of 15 minutes to a cool solution of phenyl chloroformate (6.0g, 0.038 mole) in methylene chloride (35 ml). The reaction mixture was stirred for one hour, then separated. The organic layer was dried over anhydrous magnesium sulfate, then filtered and stripped of solvent on a Rotovap. White crystals of phenyl N-ethylcarbamate weighing 6.27g were obtained having a melting point of 49°-50° C.

Workup

  1. customseparated
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-33bd110d4ee74762a070193f658d90ff
Source dataset
uspto-grants-1978_10
Patent number
US04123450

Reaction notes

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