Ethyl isocyanate → N-Dodecyl-N'-ethylurea

HRID 1380269Notes

Reaction equation

HRID 1380269 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15]>>[CH2:1]([NH:13][C:17]([NH:16][CH2:14][CH3:15])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 13583Dodecylamine

Product 1

HCID 23326344N-Dodecyl-N'-ethylurea

Conditions

Temperature
50 °C

Procedure

Dodecylamine (370 g) was placed in 80/100° fraction petroleum ether (1.5 litre) and stirred in a flask fitted with a dipping thermometer, tap funnel and reflux condenser. A mixture of ethyl isocyanate (142 g) and petroleum ether (150 ml) was run in slowly whilst external cooling was applied to the flask. The temperature was allowed to reach but not exceed 50° C. The mixture was stirred for 1 hour after the addition was complete, maintaining the temperature at about 50° C. The reaction was then allowed to cool and the copious white precipitate (which had begun to separate as soon as the isocyanate addition commenced) was filtered off, pressed well and washed with about 300 ml petroleum ether. The white mass was dried in vacuum at 50° C. to give a quantitative yield (512 g) with a melting point of 84° to 87° C. The product was not subjected to any further purification before use.

Workup

  1. customfitted with a dipping thermometer, tap funnel
  2. temperaturereflux condenser
  3. temperaturewhilst external cooling
  4. customexceed 50° C
  5. stirringThe mixture was stirred for 1 hour
  6. additionafter the addition
  7. temperatureto cool
  8. customto separate as
  9. additionsoon as the isocyanate addition
  10. filtrationwas filtered off
  11. washwashed with about 300 ml petroleum ether
  12. customThe white mass was dried in vacuum at 50° C.
  13. customto give a quantitative yield (512 g) with a melting point of 84° to 87° C
  14. customThe product was not subjected to any further purification before use

Sources & evidence

ORD record
ord-60bbd4a05be54c1abf6b4fc82a16ff0d
Source dataset
uspto-grants-1986_04
Patent number
US04581325

Reaction notes

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