Toluene → HCID 23463257, compound

HRID 903539Notes

Reaction equation

HRID 903539 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].[O:14]=[C:13]1[N:15]([CH3:16])[CH2:6][P+:3]2([CH2:1][N:15]([CH3:16])[C:13](=[O:14])[N:12]([CH3:11])[CH2:4]2)[CH2:8][N:12]1[CH3:11]

Participants

5

Reactant 3

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

Product 1

HCID 23463257HCID 23463257, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of THPC (19.06 g, 0.1 mol), 1,3-dimethylurea (17.62 g, 0.2 mol), and toluene (150 ml) was heated to reflux in an apparatus fitted with a mechanical stirrer and a Dean-Stark trap for azeotropic removal of the water. The mixture was held at reflux unitl the evolution of water ceased (4 hr); this condensation, as might be expected, required a longer reflux period and more efficient stirring to displace the last of the water than that of Example 1. Half of the 7.2 ml (100.0%) of water was collected during the first 15 min. The product, which separated during the reaction as a mass of white solids, was broken up, triturated under acetonitrile to remove a resinous by-product (4.09 g), filtered, rinsed with acetonitrile and dried, giving 26.21 g (86.3%) of 3,9-dioxo-2,4,8,10-tetramethyl-2,4,8,10-tetraaza-6-phosphoniaspiro[5.5]undecane chloride (II, R=R'=CH3, X=Cl) as a white, crystalline solid. Two recrystallizations from 2-propanol (12 ml/g) gave pure product, mp 161°-162° C. and resolidifying, then mp 217° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureto reflux in an apparatus
  3. customfitted with a mechanical stirrer
  4. customa Dean-Stark trap for azeotropic removal of the water
  5. temperatureat reflux unitl the evolution of water
  6. custom(4 hr)
  7. customthis condensation
  8. temperaturea longer reflux period
  9. customHalf of the 7.2 ml (100.0%) of water was collected during the first 15 min
  10. customThe product, which separated during the reaction as a mass of white solids
  11. customtriturated under acetonitrile
  12. customto remove a resinous by-product (4.09 g)
  13. filtrationfiltered
  14. washrinsed with acetonitrile
  15. customdried

Sources & evidence

ORD record
ord-088c859d5afc42dfa5aae4145f8cd1b5
Source dataset
uspto-grants-1980_10
Patent number
US04228100

Reaction notes

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