Ethylene carbonate → 2-Hydroxyethyl hydrogen butylcarbonimidate

HRID 1194459Notes

Reaction equation

HRID 1194459 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][O:2]1.[CH2:7]([NH2:11])[CH2:8][CH2:9][CH3:10]>>[CH2:7]([NH:11][C:1](=[O:6])[O:2][CH2:3][CH2:4][OH:5])[CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 7303Ethylene carbonateHCID 8007Butylamine

Product 1

HCID 2321242-Hydroxyethyl hydrogen butylcarbonimidateYield 89.5%

Procedure

274.8 grams of ethylene carbonate (3.12 moles) were placed in a round bottom flask equipped with stirrer, thermometer, addition funnel and reflux condenser. 228.2 grams (3.12 mole) of butylamine were charged to the addition funnel and added to the flask at a rate sufficient to maintain the flask contents at 50°-80° C. The resultant reaction product was allowed to stand overnight. Thereafter, stripping of the reaction product in a rotary evaporator gave 449.9 g of crude product. A portion of the crude product was distilled at a pressure of 2 mm Hg, and a temperature of from 124° C. to 126° C. to purify same. The HLB value of 2-hydroxyethyl 1 butyl carbamate calculated as previously described is 12.9.

Workup

  1. customequipped with stirrer
  2. additionthermometer, addition funnel
  3. temperaturereflux condenser
  4. additionadded to the flask at a rate sufficient
  5. temperatureto maintain the flask contents at 50°-80° C
  6. customThe resultant reaction product
  7. customThereafter, stripping of the reaction product in a rotary evaporator

Sources & evidence

ORD record
ord-ed2ccc3aa1c545c295cddb16a44f8efd
Source dataset
uspto-grants-1989_03
Patent number
US04814382

Reaction notes

Loading…