Ammonia → HCID 20528877, compound

HRID 2052233Notes

Reaction equation

HRID 2052233 reaction equation
N[C:2](N)=[O:3].[CH:5]1([NH:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.N>O>[CH:5]1([N:11]2[CH2:12][CH2:13][CH2:14][NH:15][C:2]2=[O:3])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 1176UreaHCID 18718N-Cyclohexyl-1,3-propanediamine

Product 1

HCID 20528877HCID 20528877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction apparatus is a 500 ml flask, equipped with thermometer, reflux condenser and magnetic stirrer. The top of the reflux condenser is connected to a bubbler containing water. Before adding the reagents, the flask is weighed. Then 30 g of urea (0.5 mols) and 156 g of N-cyclohexyl-1,3-propanediamine (1 mol) are put into the flask, which is then slowly heated. Ammonia begins to evolve. Heating is continued until 18 g of ammonia have evolved. The reaction mixture is allowed to cool to room temperature. The solid which precipitates is separated by filtration on a Buchner funnel and dried in vacuo. The weight is 78 g and the melting point is 175° C. The raw reaction product is recrystallized from boiling ethanol. The melting point of the recrystallized product is 198° C. The nitrogen content is 15.25%, whereas the theoretical value is 15.37%. The structure of the product as confirmed by a combination of elemental analysis, 13C NMR and 1H NMR is determined as follows: ##STR3## The structure of this compound has been corroborated by IR and VPO molecular weight measurements. The elemental analysis is as follows:

Workup

  1. customequipped with thermometer
  2. temperaturereflux condenser and magnetic stirrer
  3. additionBefore adding the reagents
  4. temperatureis then slowly heated
  5. temperatureHeating
  6. customThe solid which precipitates
  7. customis separated by filtration on a Buchner funnel
  8. customdried in vacuo
  9. customThe raw reaction product
  10. customis recrystallized
  11. customis 198° C

Sources & evidence

ORD record
ord-d6ba335345ca492d93c6e1085b03eea2
Source dataset
uspto-grants-1980_01
Patent number
US04183903

Reaction notes

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