1,3-Bis[3-(dimethylamino)propyl]urea

Liquid

A mixture of dimethylaminopropylamine (51.09, 0.5 mol) and urea (15.01 g, 0.25 mol) was added in a round-bottomed flask. The mixture was heated to 125°C and was refluxed for 8 h with stirring and heating. In the period of the reaction, high purity nitrogen was bubbled through the reaction solution, carrying ammonia gas out and into a sulfuric acid trap (30 wt.percent H2SO4). The product was a clear colorless liquid (58.52 g, yield: 88.65percent).[0149] Into a 2 L separable flask, 360.4 g (6.0 mol) of urea and 429.3 g (4.2 mol) of N, N’-dimethylaminopropylaminewere charged and heated at 120°C for 4 hours. Then, after confirming that ammonia gas was no longer generated, thereaction was terminated, whereupon the obtained reaction liquid was cooled, and a volatile substance was removed bymeans of a vacuum pump. As a result of the measurement by HPLC (high performance liquid chromatography) analysis(Column: TSKgel SP-2SW, manufactured by Tosoh Corporation, eluent: acetonitrile/150 mM phosphate buffer=1/9, detector: UV-8020), the obtained product was a mixture of 3-dimethylaminopropylurea and N, N’-bis(3-dimethylaminopropyl)urea, whereby 3-dimethylaminopropylurea was obtained in an amount of 843.5 g (5.8 mol), and N, N’-bis(3-dimethylaminopropyl)urea was obtained in an amount of 191.7 g (0.8 mol).Take 63.2 g of urea and mix 269 g of N, N-dimethyl-1, 3-propanediamine. 1.2 g of semicarbazide hydrochloride and 0.3 g of 50% hydrazine hydrate were added, and the temperature was raised to 110-115 C. After 5-10 min of reaction, the temperature was gradually raised to 130 C. After 1 h, the temperature was raised to 150 C, and the temperature was lowered after 1 h. unreacted N, N-dimethyl-1, 3propanediamine was distilled off under reduced pressure to give a colorless, transparent, viscous liquid product, yielding 94.8% in terms of urea. The purity of the target product in this example was more than 98% by gas chromatography.A mixture of dimethylaminopropylamine (51.09, 0.5 mol) and urea (15.01 g, 0.25 mol) was added in a round-bottomed flask. The mixture was heated to 125C and was refluxed for 8 h with stirring and heating. In the period of the reaction, high purity nitrogen was bubbled through the reaction solution, carrying ammonia gas out and into a sulfuric acid trap (30 wt.% H2SO4). The product was a clear colorless liquid (58.52 g, yield: 88.65%).General procedure: A mixture of the ditertiary amine (Compound 2) (11.52 g, 0.05 mol) and water (15 g) was charged into a reaction flask fitted with thermometer, stirrer and reflux condenser and heated to 65°C. Epichlorohydrin (4.63 g, 0.05 mol) was then added into the reactor. The temperature was gradually raised to 76°C and the reaction was carried out for 3 h. After the reaction, the resulted product was purified via vacuum distillation to remove unreacted reactants. The product was a clear and yellowish liquid (15.10 g, yield: 93.49percent).General procedure: A mixture of the ditertiary amine (Compound 2) (11.52 g, 0.05 mol) and water (15 g) was charged into a reaction flask fitted with thermometer, stirrer and reflux condenser and heated to 65°C. Epichlorohydrin (4.63 g, 0.05 mol) was then added into the reactor. The temperature was gradually raised to 76°C and the reaction was carried out for 3 h. After the reaction, the resulted product was purified via vacuum distillation to remove unreacted reactants. The product was a clear and yellowish liquid (15.10 g, yield: 93.49percent).A mixture of the ditertiary amine (Compound 2) (11.52 g, 0.05 mol) and water (15 g) was charged into a reaction flask fitted with thermometer, stirrer and reflux condenser and heated to 65°C. Epichlorohydrin (4.63 g, 0.05 mol) was then added into the reactor. The temperature was gradually raised to 76°C and the reaction was carried out for 3 h. After the reaction, the resulted product was purified via vacuum distillation to remove unreacted reactants. The product was a clear and yellowish liquid (15.10 g, yield: 93.49percent).General procedure: A mixture of the ditertiary amine (Compound 2) (11.52 g, 0.05 mol) and water (15 g) was charged into a reaction flask fitted with thermometer, stirrer and reflux condenser and heated to 65°C. Epichlorohydrin (4.63 g, 0.05 mol) was then added into the reactor. The temperature was gradually raised to 76°C and the reaction was carried out for 3 h. After the reaction, the resulted product was purified via vacuum distillation to remove unreacted reactants. The product was a clear and yellowish liquid (15.10 g, yield: 93.49percent).[0149] Into a 2 L separable flask, 360.4 g (6.0 mol) of urea and 429.3 g (4.2 mol) of N, N?-dimethylaminopropylaminewere charged and heated at 120°C for 4 hours. Then, after confirming that ammonia gas was no longer generated, thereaction was terminated, whereupon the obtained reaction liquid was cooled, and a volatile substance was removed bymeans of a vacuum pump. As a result of the measurement by HPLC (high performance liquid chromatography) analysis(Column: TSKgel SP-2SW, manufactured by Tosoh Corporation, eluent: acetonitrile/150 mM phosphate buffer=1/9, detector: UV-8020), the obtained product was a mixture of 3-dimethylaminopropylurea and N, N?-bis(3-dimethylaminopropyl)urea, whereby 3-dimethylaminopropylurea was obtained in an amount of 843.5 g (5.8 mol), and N, N?-bis(3-dimethylaminopropyl)urea was obtained in an amount of 191.7 g (0.8 mol).

Intermediates

Paints and coatings

1,000,000 - 10,000,000 lb

Molecular Weight:230.35
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:8
Exact Mass:230.21066147
Monoisotopic Mass:230.21066147
Topological Polar Surface Area:47.6
Heavy Atom Count:16
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes