Formaldehyde → 2-Thia-1,3,5-triaza-7-phosphaadamantane 2,2-dioxide

HRID 1579946Notes

Reaction equation

HRID 1579946 reaction equation
O[CH2:2][P:3]([CH2:6]O)[CH2:4]O.C=O.[S:10]([NH2:14])([NH2:13])(=[O:12])=[O:11].[CH2:15]1N2CN3CN(C2)[CH2:17][N:16]1C3>O>[N:13]12[CH2:17][N:16]3[CH2:2][P:3]([CH2:6][N:14]([CH2:15]3)[S:10]1(=[O:12])=[O:11])[CH2:4]2

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 4101HexamethylenetetramineHCID 76001Tris(Hydroxymethyl)PhosphineHCID 82267Sulfamide

Product 1

HCID 218292932-Thia-1,3,5-triaza-7-phosphaadamantane 2,2-dioxideYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tris(hydroxymethyl)phosphine (3.9 g, 80%, 0.025 moles) was dissolved in formalin (20 ml, 40%, 0.267 moles) and water (20 ml). Sulfamide (2.4 g, 0.025 mole) and hexamethylenetetramine (3.5 g, 0.025 mole) were added together and dissolved in the solution at room temperature. The solution heated up slightly and over the next twenty-four hours a precipitate formed. Filtration, dissolution of the solid in 4 successive 30 ml acetone washes and evaporation of the acetone yielded 3.42 g of crude 2-thia-1,3,5-triaza-7-phosphaadamantane 2,2-dioxide (66% yield) [mp 274°-5° (water)].

Workup

  1. dissolutiondissolved in the solution at room temperature
  2. temperatureThe solution heated up slightly and over the next twenty-four hours a precipitate
  3. customformed
  4. filtrationFiltration, dissolution of the solid
  5. customin 4 successive 30 ml acetone washes and evaporation of the acetone

Sources & evidence

ORD record
ord-073edc8f41924737b6357787a100ba9b
Source dataset
uspto-grants-1976_01
Patent number
US03932390

Reaction notes

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