Diethylamine → Chloromethyl diethylcarbamate

HRID 1376126Notes

Reaction equation

HRID 1376126 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8]>CCCCCCC>[CH2:7]([N:9]([CH2:10][CH3:11])[C:2](=[O:3])[O:4][CH2:5][Cl:6])[CH3:8]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 62754Chloromethyl chloroformate

Product 1

HCID 14800940Chloromethyl diethylcarbamateYield 911.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

To a stirred solution of chloromethyl chloroformate (7.09 g, 5.5 mmol) in heptane (100 mL) at −20° C. add a solution of diethylamine (10.4 g, 14.7 mmol) in heptane (50 mL), dropwise. Maintain the internal temperature between −15° C. to −5° C. and after 1 h quench the reaction with water. Separate the layers and wash the organic phase with 10% aqueous HCl, water and NaHCO3 solution. Dry the organic layer (MgSO4), filter and concentrate under reduced pressure to obtain 8.3 g of the title compound.

Workup

  1. temperatureMaintain the internal temperature between −15° C. to −5° C.
  2. customafter 1 h quench
  3. customthe reaction with water
  4. customSeparate the layers
  5. washwash the organic phase with 10% aqueous HCl, water and NaHCO3 solution
  6. dry with materialDry the organic layer (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-03a1ffd4fd2e47e280c2d0b714b63544
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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