N,N'-Dimethylurea → HCID 21501253, compound

HRID 1576287Notes

Reaction equation

HRID 1576287 reaction equation
[CH3:1][NH:2][C:3]([NH:5][CH3:6])=[O:4].[P:7]([O:16]CCCl)([O:12]CCCl)[O:8]CCCl.[CH2:20]([CH:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH:23]=O)[CH3:21]>C1CCCCC1.O>[CH3:1][N:2]([CH:23]([P:7](=[O:8])([OH:12])[OH:16])[CH:22]([CH2:20][CH3:21])[CH2:25][CH2:26][CH2:27][CH3:28])[C:3]([NH:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 7293N,N'-DimethylureaHCID 8783Tris(2-chloroethyl) phosphiteHCID 312412-Ethylhexanal

Product 1

HCID 21501253HCID 21501253, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of 88.1g (1.0 mole) of 1,3-dimethylurea, 269.5g (1.0 mole) of tris(2-chloroethyl) phosphite, and 135g (1.05 moles) of 2-ethylhexaldehyde is warmed at 105°-110° for 2 hr, giving a clear colorless solution: 31P nmr -30.8 and -28.2 ppm (~2:1 areas). Four-fifths of the reaction mixture is dissolved in 200ml of cyclohexane containing 34.5g of H2O, and the mixture is warmed at 82° for 0.5 hr. Filtration after cooling, and extraction of the solid with hot acetonitrile gives 54.7g of white solid (100.8g more separates from the filtrate while standing): mp 184°-186° dec; 31P nmr (CD3SOCD3) -23.5 ppm(m); 1H nmr δ9.8 (broad, 2, OH), 4.4 (d of d, 1, J = 10 and 20Hz, PCH), 2.7 (s, 3, NCH3), 2.5 (s, 3, NCH3), 0.5-2.0 (broad, 15, hexyl); acidity 1.985 equiv/mole, pK1 = 1.76, pK2 = 5.29.

Workup

  1. temperatureis warmed at 105°-110° for 2 hr
  2. customgiving a clear colorless solution
  3. temperaturethe mixture is warmed at 82° for 0.5 hr
  4. filtrationFiltration
  5. temperatureafter cooling
  6. extractionextraction of the solid with hot acetonitrile

Sources & evidence

ORD record
ord-20504452bb244253984318d528995a7a
Source dataset
uspto-grants-1976_09
Patent number
US03980618

Reaction notes

Loading…