Carbamic acid, ethyl ester → 5-(2-Ethylhexyl) oxymethyl-2-oxazolidinone

HRID 326404

Reaction equation

[C:1](=[O:6])([O:3][CH2:4][CH3:5])[NH2:2].C([O:11][CH2:12][CH:13]([CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][CH3:17])C1OC1.[C:20]([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>CN(CC1C=CC=CC=1)C>[CH2:18]([CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][O:11][CH2:5][CH:4]1[O:3][C:1](=[O:6])[NH:2][CH2:20]1)[CH3:19]

Participants

Conditions

Temperature: 160 °C

Procedure

8.9 g (0.10 mole) of ethyl carbamate was dissolved in 18.6 g (0.10 mole) of 2-ethylhexyl glycidyl ether. After adding 0.41 g of N, N-dimethylbenzylamine and 0 63 g of di-n-butyltin dilaurate, the solution was heated at 160° C. for 1 hour while blowing nitrogen gas into the reaction mixture. The product was distilled under reduced pressure to give 20.0 g (88% of theory) of 5-(2-ethylhexyl) oxymethyl-2-oxazolidinone.

Workup

distillationThe product was distilled under reduced pressure

Sources & evidence

ORD record: ord-c388f809cda045e386d237f8b7d3cc00
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268484

Linked notes

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