1,10-Decanediamine → 1-n-Butyl-3-(10'-aminodecyl) urea

HRID 1658466Notes

Reaction equation

HRID 1658466 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16]>CCOCC>[CH2:13]([NH:17][C:18]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:19])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 13171,10-DecanediamineHCID 8110Butyl isocyanate

Product 1

HCID 543820331-n-Butyl-3-(10'-aminodecyl) ureaYield 82.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 500 ml flask protected with a soda lime tube is placed 10 g (0.058 mole) 1,10-diamino decane and 150 ml ether. A solution of 2.5 g (0.025 mole)n-butyl isocyanate in 25 ml ether is added and the reaction mixture stirred 1 hour. The precipitate is filtered, washed with ether, and dried to 15 g weight. Recrystallization from a mixture of 200 ml alcohol and 100 ml water gives 5.6 g white solids. An analytical sample recrystallized from acetonitrile melts at 83°-84.5°C.

Workup

  1. customIn a 500 ml flask protected with a soda lime tube
  2. filtrationThe precipitate is filtered
  3. washwashed with ether
  4. customdried to 15 g weight
  5. customRecrystallization
  6. additionfrom a mixture of 200 ml alcohol and 100 ml water

Sources & evidence

ORD record
ord-844853bf524e418f82c8011d4e045a98
Source dataset
uspto-grants-1976_06
Patent number
US03965015

Reaction notes

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