Urea → HCID 131731081, compound

HRID 1912215Notes

Reaction equation

HRID 1912215 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([Cl:5])=[O:4].C(N(CC)CC)C.[CH3:14][CH:15]([NH2:30])[CH2:16][O:17][CH2:18][CH:19]([O:21][CH2:22][CH:23]([O:25][CH2:26][CH:27]([NH2:29])[CH3:28])[CH3:24])[CH3:20].NC(N)=O>O1CCOCC1>[CH3:1][N:2]([CH3:6])[C:3]([Cl:5])=[O:4].[CH3:14][CH:15]([NH2:30])[CH2:16][O:17][CH2:18][CH:19]([O:21][CH2:22][CH:23]([O:25][CH2:26][CH:27]([NH2:29])[CH3:28])[CH3:24])[CH3:20]

Participants

6

Reactant 4

HCID 1176UreaHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 15131492Jeffamine

Product 1

HCID 131731081HCID 131731081, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

15.0 g (139.5 mmol) of N,N-dimethylcarbamoyl chloride and 80 mL dioxane were added to a 250 mL two-necked flask with a reflux condenser. Then 13.66 g (135 mmol) triethylamine and 14.88 g (approx. 63 mmol) Jeffamine® D-230 (Huntsman) were added. After the slight exothermic evolution of heat subsided, the mixture was stirred for 3 h at 80° C. and for 1 h at 100° C., where a milky yellowish suspension slowly formed. The suspension obtained in this way was filtered twice through a fluted filter. The solvent was driven off on the rotary evaporator at 60° C. Then the product was purified with stirring for 2 h at 100° C. and 0.3 mbar. Approximately 17.0 g of an orange-red, viscous liquid was obtained, with a calculated “urea equivalent weight” of approx. 191 g/eq.

Workup

  1. addition(Huntsman) were added
  2. temperatureAfter the slight exothermic evolution of heat
  3. customwhere a milky yellowish suspension slowly formed
  4. customThe suspension obtained in this way
  5. filtrationwas filtered twice through
  6. filtrationa fluted filter
  7. customThe solvent was driven off on the rotary evaporator at 60° C
  8. customThen the product was purified
  9. stirringwith stirring for 2 h at 100° C.
  10. customApproximately 17.0 g of an orange-red, viscous liquid was obtained

Sources & evidence

ORD record
ord-e59423d8262442928c832c5796439e7a
Source dataset
uspto-grants-2013_12
Patent number
US08608899B2

Reaction notes

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