1,3-Propanediamine → HCID 54564932, compound

HRID 1658465Notes

Reaction equation

HRID 1658465 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[CH2:6]([N:18]=[C:19]=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CCOCC>[CH2:6]([NH:18][C:19]([NH:1][CH2:2][CH2:3][CH2:4][NH2:5])=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 77873Dodecane, 1-isocyanato-

Product 1

HCID 54564932HCID 54564932, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 500 ml flask protected by a soda lime tube is placed 8 g (0.108 mole) of 1,3-diaminopropane in 150 ml ether. The solution is stirred in an ice bath for 30 minutes during the slow addition of a solution of 11.1 g (0.0525 mole) dodecyl isocyanate in 50 ml ether. After standing 15 minutes, the white solid precipitate was separated by filtration, washed well with ether, and dried. The 15.2 g solid obtained is crystallized from a mixture of 1100 ml alcohol and 600 ml water. From the 10.7 g which dissolved, there is obtained 9.2 g recrystallized product. An analytical sample recrystallized from acetonitrile melted at 97°-98°C.

Workup

  1. customIn a 500 ml flask protected by a soda lime tube
  2. customthe white solid precipitate was separated by filtration
  3. washwashed well with ether
  4. customdried

Sources & evidence

ORD record
ord-037ef8493ca74c09b33b586037f07389
Source dataset
uspto-grants-1976_06
Patent number
US03965015

Reaction notes

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