N,N-Dimethyl-1,3-propanediamine → Urea, N,N''-1,6-hexanediylbis[N'-[3-(dimethylamino)propyl]-

HRID 223277

Reaction equation

HRID 223277 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][NH2:7])[CH3:3].[CH2:8]([N:17]=[C:18]=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16]>C(Cl)Cl>[N:2]([CH2:4][CH2:5][CH2:6][NH:7][C:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:17][C:18]([NH:7][CH2:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[O:19])=[O:16])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 13192Hexamethylene diisocyanate

Product 1

HCID 335058Urea, N,N''-1,6-hexanediylbis[N'-[3-(dimethylamino)propyl]-Yield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

204.3 g of dimethylaminopropylamine are added dropwise to a solution of 168.2 g of hexamethylene diisocyanate in 100 ml of methylene chloride and the mixture is refluxed overnight, in the process of which crystals precipitate. The crystals are filtered with suction at room temperature, washed with CH2Cl2 and dried. Recrystallisation from a mixture of 1000 ml of acetone and 800 ml of ethanol yields 221.0 g (59.3%) of product with a melting point of 159° C. Tritration: 2 equivalents=376.7 g (theory 372.6 g).

Workup

  1. temperaturethe mixture is refluxed overnight, in the process of which crystals
  2. customprecipitate
  3. filtrationThe crystals are filtered with suction at room temperature
  4. washwashed with CH2Cl2
  5. customdried
  6. customRecrystallisation
  7. additionfrom a mixture of 1000 ml of acetone and 800 ml of ethanol

Sources & evidence

ORD record
ord-158ec3ab0f664ddd8feb3e98ca716c91
Source dataset
uspto-grants-1982_10
Patent number
US04352913

Linked notes

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