Ethylene carbonate → 4-(Dec-1-yl)-2-oxo-1,3-oxazolidine

HRID 1087752Notes

Reaction equation

HRID 1087752 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][OH:4].[C:15]1(=O)OCC[O:16]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:5]([CH:2]1[CH2:3][O:4][C:15](=[O:16])[NH:1]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 35322502-Amino-1-dodecanol

Product 1

HCID 102201904-(Dec-1-yl)-2-oxo-1,3-oxazolidineYield 96.56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

26.465 g of 2-aminododecanol and 12.32 g of ethylene carbonate were heated at approximately 110° C. for 48 hours (preparation of the cyclic urethanes can be carried out without a solvent or in toluene solution)as a solvent. The reaction was followed by tlc and at the completion of the reaction the contents were cooled, dissolved in ethyl acetate and the organic solution was washed with brine and water. After drying, the filtrate was concentrated and the oily residue was kugelrohr distilled to give 27.33 g (96.56%) of colorless liquid, which slowly solidified, m.p. 31.5-32.5° C.

Workup

  1. customat the completion of the reaction the contents
  2. temperaturewere cooled
  3. washthe organic solution was washed with brine and water
  4. customAfter drying
  5. concentrationthe filtrate was concentrated
  6. distillationthe oily residue was kugelrohr distilled

Sources & evidence

ORD record
ord-4feeae0fd4a34fed8c3f6a25598ee9a4
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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