Toluene → 69248-03-9

HRID 903529Notes

Reaction equation

HRID 903529 reaction equation
[CH2:1]([P+:3]([CH2:8]O)([CH2:6]O)[CH2:4]O)O.[Cl-:10].[CH3:11][NH:12][C:13]([NH:15][CH3:16])=[O:14].C1(C)C=CC=CC=1>O>[Cl-:10].[CH3:11][N:12]([CH2:8][P+:3]([CH2:1][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])([CH2:4][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])[CH2:6][N:12]([CH3:11])[C:13]([NH:15][CH3:16])=[O:14])[C:13]([NH:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7293N,N'-DimethylureaHCID 31298Tetrakis(hydroxymethyl)phosphonium chloride

Product 1

HCID 15331469248-03-9Yield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of THPC (9.53 g, 0.05 mol), 1,3-dimethylurea (17.62 g, 0.20 mol), and toluene (75 ml) was heated to reflux in an apparatus fitted with a Dean-Stark trap for azeotropic removal of the water. The mixture was held at reflux until the evolution of water ceased; 3.7 ml (0.20 mol) was collected in 1 hr., and no more passed over in the next hr. The product, which had separated during the reaction as a mass of white solids, was broken up, triturated under toluene, filtered, and dried, giving 22.88 g (97.2%) of tetrakis(1,3-dimethylureidomethyl)phosphonium chloride (I, R=R'=CH3, R"=H, X=Cl) as a white crystalline solid, mp 187°-189° C. dec. Two recrystallizations from 2-propanol (8 ml/g), followed by drying under vacuum for 2 hr at 56° C. (acetone), gave a 1:1 solvate of the product and 2-propanol, mp 194°-194.5° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureto reflux in an apparatus
  3. custom3.7 ml (0.20 mol) was collected in 1 hr
  4. customThe product, which had separated during the reaction as a mass of white solids
  5. customtriturated under toluene
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-10bc86cfd624499a93452320c37592da
Source dataset
uspto-grants-1980_10
Patent number
US04228100

Reaction notes

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