Ethyl chloroformate → Ethyl 2,2-dimethoxyethylcarbamate

HRID 1842705Notes

Reaction equation

HRID 1842705 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH2:7].Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12]>O.C1(C)C=CC=CC=1>[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH:7][C:11](=[O:12])[O:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10921057Ethyl 2,2-dimethoxyethylcarbamateYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaOH (578.4 g, 14.46 mol) in H2O (2 L) was added to a solution of 2,2-dimethoxyethanamine (800 g, 7.6 mol) in toluene (2 L) and the resulting mixture was cooled to 0° C. using an ice bath. Ethyl chloroformate (825 g, 7.6 mol) was added dropwise while keeping the temperature near 10° C. The mixture was then stirred at r.t. overnight. The phases were then separated and the aqueous solution was saturated with solid NaCl. This solution was then extracted with toluene (1.25 L×3). The combined organic solutions were dried (Na2SO4) and concentrated in vacuo to give the title compound (1.123 kg, 83%) as colorless oil; 1H NMR: (CDCl3) 1.17 (3H, t), 3.14 (2H, s), 3.32 (6H, s), 4.02-4.07 (2H, m), 4.30 (1H, t).

Workup

  1. customnear 10° C
  2. customThe phases were then separated
  3. extractionThis solution was then extracted with toluene (1.25 L×3)
  4. dry with materialThe combined organic solutions were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5e11497e7c94f6ba25d8e90d0560ba9
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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