Dimethylformamide → Phosphonic acid (dimethylamino(methylene))

HRID 1576056Notes

Reaction equation

HRID 1576056 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[P:6]([OH:9])([OH:8])[OH:7].P(Cl)(Cl)Cl>O>[CH3:1][N:2]([CH3:5])[CH:3]([P:6]([OH:9])(=[O:7])[OH:8])[P:6]([OH:9])(=[O:8])[OH:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 107909Phosphorous acid

Product 1

HCID 122520Phosphonic acid (dimethylamino(methylene))Yield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

73.1 parts of dimethyl formamide were mixed with 41 parts by phosphorous acid and this mixture was reacted with 137.3 parts of phosphorus trichloride at about 70°C. A viscous mass was formed, which after about an hour was treated with 180 parts of water. The solution so obtained was filtered and treated with acetone. A precipitate was formed which was further treated as described in Example 1. N,N-dimethyl-1-aminomethane-1,1-diphosphonic acid was obtained in a yield of 76%, based on PCl3.

Workup

  1. customA viscous mass was formed
  2. customThe solution so obtained
  3. filtrationwas filtered
  4. additiontreated with acetone
  5. customA precipitate was formed which
  6. additionwas further treated

Sources & evidence

ORD record
ord-aabf04f12de0420fbebc4dab97d29ef4
Source dataset
uspto-grants-1976_09
Patent number
US03979385

Reaction notes

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