N,N'-Dimethylurea → HCID 21501253, compound

HRID 1729749Notes

Reaction equation

HRID 1729749 reaction equation
CNC(NC)=O.[P:7]([O:16]CCCl)([O:12]CCCl)[O:8]CCCl.C(C(CCCC)C=O)C.ClCCOP1(=O)[CH:37]([CH:38]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:39][CH3:40])[N:36]([CH3:45])[C:35](=[O:46])[N:34]1[CH3:47]>C1CCCCC1.O>[CH3:45][N:36]([CH:37]([P:7](=[O:8])([OH:12])[OH:16])[CH:38]([CH2:39][CH3:40])[CH2:41][CH2:42][CH2:43][CH3:44])[C:35]([NH:34][CH3:47])=[O:46]

Participants

7

Reactant 4

HCID 7293N,N'-DimethylureaHCID 8783Tris(2-chloroethyl) phosphiteHCID 312412-EthylhexanalHCID 21501258HCID 21501258, compound

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 containing 2-(2-chloroethoxy)-1,4-dimethyl-3-(3-heptyl)-1,4,2-diazaphospholidin-5-one-2-oxide, as an intermediate ester product, 31P nmr-30.8. 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 δ 9.8 (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-957f60a3ace443cf9abf8147989bbcba
Source dataset
uspto-grants-1976_11
Patent number
US03989727

Reaction notes

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