Diethylamine → HCID 74217918, compound

HRID 1514030Notes

Reaction equation

HRID 1514030 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[OH-].[Na+].[CH2:8]([O:14][C:15](Cl)=[O:16])[CH2:9][CH:10]=[CH:11][CH2:12][CH3:13]>C(OCC)C>[CH2:8]([O:14][C:15](=[O:16])[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:9][CH:10]=[CH:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 54291304Chloroformic acid hex-3-enyl ester

Product 1

HCID 74217918HCID 74217918, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Diethylamine (9.1 g, 125 mmol, 1.25 equiv.) was added to a 2%-aqueous NaOH-solution (200 ml) and the resulting mixture was cooled to 0° C. (icebath). At this temperature chloroformic acid hex-3-enyl ester (16.2 g, 100 mmol) in diethyl ether (200 ml) was added over a period of 35 min. After complete addition, the cooling bath was removed and stirring was continued for 1.5 h. The mixture was acidified with 2N aqueous HCl-solution, the phases separated and the organic phase was washed with brine and dried over MgSO4. The crude product was purified via fractionated distillation (74-76° C./0.05 mbar) to yield 18.2 g (92%) of product.

Workup

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. customthe phases separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. distillationThe crude product was purified via fractionated distillation (74-76° C./0.05 mbar)

Sources & evidence

ORD record
ord-3e3457c745664905b65a2842fc51d625
Source dataset
uspto-grants-2012_07
Patent number
US08222200B2

Reaction notes

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